WO2008019068A2 - Compositions et procédés de production chimiques - Google Patents

Compositions et procédés de production chimiques Download PDF

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Publication number
WO2008019068A2
WO2008019068A2 PCT/US2007/017350 US2007017350W WO2008019068A2 WO 2008019068 A2 WO2008019068 A2 WO 2008019068A2 US 2007017350 W US2007017350 W US 2007017350W WO 2008019068 A2 WO2008019068 A2 WO 2008019068A2
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pfp
vdf
composition
mole
grams
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PCT/US2007/017350
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WO2008019068A3 (fr
Inventor
Bruno Ameduri
Stephan Brandstadter
George K. Kostov
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Great Lakes Chemical Corporation
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Publication of WO2008019068A2 publication Critical patent/WO2008019068A2/fr
Publication of WO2008019068A3 publication Critical patent/WO2008019068A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine

Definitions

  • the present disclosure relates in general to the field of halogenated compositions and there uses. More particularly the present disclosure relates to the production of polymeric compositions including, but not limited to, copolymers as well as terpolymers and other oligomers. These compositions can be comprised by theromoplastics and/or elastomers, for example.
  • compositions that include monomer units with the monomer units being derived from monomers such as PFP for example.
  • Exemplary processes can include the copolymerization of PFP with other monomers.
  • FIG. 1A depicts at least one implementation of a process according to exemplary embodiments.
  • Fig. 1 is analytical data of a composition according to an embodiment.
  • Fig. 2 is analytical data of a composition according to an embodiment.
  • Fig. 3 is analytical data of a composition according to an embodiment.
  • Fig. 4 is analytical data of a composition according to an embodiment.
  • Fig. 5 is analytical data of a composition according to an embodiment.
  • Fig. 6 is analytical data of a composition according to an embodiment.
  • Fig. 7 is analytical data of a composition according to an embodiment.
  • Fig. 8 is analytical data of a composition according to an embodiment.
  • Fig. 9 is analytical data of a composition according to an embodiment.
  • Fig. 10 is analytical data of a composition according to an embodiment.
  • Fig. 11 is analytical data of a composition according to an embodiment.
  • Fig. 12 is analytical data of a composition according to an embodiment.
  • Fig. 13 is analytical data of a composition according to an embodiment.
  • Fig. 14 is analytical data of a composition according to an embodiment.
  • Fig. 15 is analytical data of a composition according to an embodiment.
  • Fig. 16 is analytical data of a composition according to an embodiment.
  • Fig. 17 is analytical data of a composition according to an embodiment.
  • Fig. 18 is analytical data of a composition according to an embodiment.
  • Fig. 19 is analytical data of a composition according to an embodiment.
  • Fig. 20 is analytical data of a composition according to an embodiment.
  • Fig. 21 is analytical data of a composition according to an embodiment.
  • Fig. 22 is analytical data of a composition according to an embodiment.
  • Fig. 23 is analytical data of a composition according to an embodiment.
  • Fig. 24 is analytical data of a composition according to an embodiment.
  • Fig. 25 is analytical data of a composition according to an embodiment.
  • Fig. 26 is analytical data of a composition according to an embodiment.
  • Fig. 27 is analytical data of a composition according to an embodiment.
  • Fig. 28 is analytical data of a composition according to an embodiment.
  • Fig. 29 is analytical data of a composition according to an embodiment.
  • Fig. 30 is analytical data of a composition according to an embodiment.
  • Fig. 31 is analytical data of a composition according to an embodiment.
  • Fig. 32 is analytical data of a composition according to an embodiment.
  • Fig. 33 is analytical data of a composition according to an embodiment.
  • Fig. 34 is analytical data of a composition according to an embodiment.
  • Fig. 35 is analytical data of a composition according to an embodiment.
  • Fig. 36 is analytical data of a composition according to an embodiment.
  • Fig. 37 is analytical data of a composition according to an embodiment.
  • Fig. 38 is analytical data of a composition according to an embodiment.
  • Fig. 39 is analytical data of a composition according to an embodiment.
  • Fig. 40 is analytical data of a composition according to an embodiment.
  • Fig. 41 is analytical data of a composition according to an embodiment.
  • Fig. 42 is analytical data of a composition according to an embodiment.
  • Fig. 43 is analytical data of a composition according to an embodiment.
  • Fig. 44 is analytical data of a composition according to an embodiment.
  • Fig. 45 is analytical data of a composition according to an embodiment.
  • Fig. 46 is analytical data of a composition according to an embodiment.
  • Fig. 47 is analytical data of a composition according to an embodiment.
  • Fig. 48 is analytical data of a composition according to an embodiment.
  • system 10 can include a reactor vessel 8 coupled to both a product vessel 9 as well as reactant vessels 2, 4, and 6.
  • Vessel 8 can also be coupled to catalyst and/or initiator vessel 3.
  • Reactor vessel 8 can be configured to maintain a desired temperature and/or pressure within its' contents.
  • Vessel 8 can be constructed of materials that may be considered relative inert to hydrofluorocarbons as well as hydrofluorocarbon reactants.
  • vessel 8 can include an autoclave.
  • Vessel 8 can be coupled to a pressure control device such as a vacuum pump.
  • Vessel 8 may be coupled to the remaining vessels using coupling and/or transfer devices and/or techniques known in the industry.
  • vessels 2, 3, 4, 6, and 9 may well be coupled to vessel 8 via tubing and/or pipe.
  • the tubing and/or pipe can be inert to reactants, catalysts, initiators and/or products.
  • the tubing and/or pipe can be constructed on metal alloys such as stainless steel and/or the tubing and/or pipe may be constructed of or configured to have an interior coating of silicon.
  • Exemplary autoclaves can be constructed of Hastelloy ® (HC-276) (Haynes International, Inc., Kokomo, IN). Vessels and conduits of glass may be utilized.
  • Carius tubes of borosilicate glass may be utilized as vessel 8.
  • a pressure differential may be provided between vessels 2, 3, 4, 6, and 9, and 8 to facilitate the transfer of the composition and/or fluid from vessel to vessel.
  • the pressure differential may be facilitated by using a pump and/or vacuum.
  • a composition such as a catalyst and/or initiator may be provided to vessel 8.
  • the composition may take the form of a solution and/or mixture of one or more compounds.
  • the composition can include a catalyst and/or initiator and a fluid, in gas or liquid form.
  • the fluid can include 1 ,1 ,1 ,3,3-pentafluorobutane (PFB) and/or acetonitrile.
  • the composition provided to vessel 8, with or without the fluid can include 2,5-dimethyl-2,5- di(tert-butylperoxy)hexane marketed by Akzo-Nobel as Trigonox 101.
  • the composition can also be, either alone or in combination with another composition such as Trigonox 101 , di-tertbutylperoxide (DTBP).
  • DTBP di-tertbutylperoxide
  • Monomers from vessels 2, 4, and/or 6 may then be provided to vessel 8.
  • the monomers from vessels 2, 4, and/or 6 may be exposed to one another within vessel 8 to form a composition comprising monomer units.
  • the composition can be an oligomer for example, and/or a homopolymer of repeating oligomers units.
  • the composition may also be a copolymer.
  • the composition can include monomer units that are consistent with the monomers being used during production to form the composition.
  • the monomer PFP can be exposed to the monomer CTFE to form a composition having monomer units of PFP and CTFE.
  • An example composition including these monomer units is shown in Fig. 37.
  • Compositions can be produced from more than two monomers and can include more than two different monomer units.
  • production can include providing the monomer PFP to vessel 8 from vessel 2. Additional monomer, such as VDF may be provided to vessel 8 from vessel 4. According to exemplary embodiments an initial mole ratio of PFP/VDF provided to vessel 8 can be from about 1/10 to about 10/1 , from about 1/1 to about 4/1 , and/or from about 1/1 to about 3/1. Vessel 8 can then be heated to about 130 0 C. Upon workup of a reaction mixture, a composition that can include monomer units of PFP and VDF can be acquired that includes a mole ratio of monomer units of PFP/VDF of from about 1/2 to about 1/20, from about 1/2 to about 1/8, and/or from about 1/2 to about 1/5.
  • a mixture of Trigonox 101 and PFB may be provided to vessel 8 from vessel 3 and copolymerization can include providing the monomer PFP to vessel 8 from vessel 2 and the additional monomer HFP to vessel 8 from vessel 4.
  • an initial mole ratio of PFP/HFP provided to vessel 8 can be at least about 2/1.
  • Vessel 8 can then be heated to about 130 0 C.
  • a composition that includes monomer units PFP and HFP can be acquired that includes a mole ratio of monomer units of PFP/HFP of at least about 1 :6.
  • an additional monomer may be added to vessel 8 from vessel 6.
  • This monomer can be added to vessel 8 in addition to the monomer added to vessel 8 from vessels 2 and 4.
  • the monomer HFP may be added to vessel 8 in addition to the monomers PFP and VDF added from vessels 2 and 4 respectively.
  • the mole ratios of PFP/VDF/HFP can be from about 1/1/1 to about 5/3/2, from about 1/1/1 to about 3/6/4, and/or from about 2/5/3 to about 5/3/2, as well as include about 1/5/4.
  • a composition comprising monomer units of PFP, VDF 1 and HFP can be recovered.
  • the composition can include a mole ratio PFP/ VDF/ HFP monomer units of from about 1/4/2 to about 1/32/3, and/or from about 1/6/3 to about 1/7/2, as well as 2/7/3.
  • a mixture of Trigonox 101 and acetonitrile may be provided to vessel 8 from vessel 3 and copolymerization can include providing the monomer PFP to vessel 8 from vessel 2 and the additional monomer provided from vessel 4 to vessel 8 can be tert-butyl trifluoromethyl acrylate (TFMA).
  • TFMA tert-butyl trifluoromethyl acrylate
  • an initial mole ratio of PFP /TFMA provided to vessel 8 can be from about 1/1 to about 6/1 and/or from about 1/1 to about 4/1.
  • Vessel 8 can then be heated to about 130 0 C.
  • a composition that includes monomer units of PFP and TFMA can be acquired that includes a mole ratio of monomer units of PFP/TFMA of from about 1/6 to about 1/50 and/or from about 0.2/9.8 to about 1/9.
  • an additional monomer may be added to vessel 8 from vessel 6.
  • This monomer can be added to vessel 8 in addition to the monomer added to vessel 8 from vessels 2 and 4.
  • the monomer PFP may be added to vessel 8 in addition to the monomers TFMA and VDF added from vessels 4 and 2 respectively.
  • vessel 3 may be configured to provide a composition that includes DTBP, Trigonox 101 , and PFB to vessel 8 prior to the addition of PFP, TFMA and/or VDF from vessels 6, 2, and 4 respectively.
  • the mole ratios of PFP/TFMA/VDF can be from about 1/1/2 to about 69/1/18 and/or from about 5/4/1 to about 7/2/1 and include from about 2/7/1 to about 2.5/5/2.5.
  • a composition (terpolymer) comprising monomer units of PFP, TFMA, and VDF can be recovered.
  • the composition can include a mole ratio of PFP/TFMA/VDF monomer units of from about 1/2/2 to about 1/15/13 and/or from about 1/6/3 to about 5/4/1 as well as from about 1/4/5 to about 1/3/6 and 1/4/5.
  • a mixture of Trigonox 101 and acetonitrile may be provided to vessel 8 from vessel 3 and copolymerization can include providing the monomer PFP to vessel 8 from vessel 2 and the additional monomer provided from vessel 4 to vessel 8 can be perfluoromethylvinyl ether (PMVE).
  • a mole ratio of PFP/PMVE provided to vessel 8 can be from about 1/1 to about 4/1 and/or from about 1/1 to about 3/1.
  • Vessel 8 can then be heated to about 130 0 C.
  • a composition that includes monomer units of PFP and PMVE can be acquired that includes a mole ratio of monomer units of PFP/PMVE of from about 2/7 to about 1/50.
  • an additional monomer may be added to vessel 8 from vessel 6.
  • This monomer can be added to vessel 8 in addition to the monomer added to vessel 8 from vessels 2 and 4.
  • the monomer VDF may be added to vessel 8 in addition to the monomers PFP and PMVE added from vessels 2 and 4 respectively.
  • PFP/VDF/PMVE can be from about 2/1/1 to about 10/1/2.
  • a composition comprising monomer units of PFP, PMVE, and VDF can be recovered.
  • the composition can include a mole ratio of PFP/VDF/PMVE monomer units of from about 1/3/1 to about 1/20/8.
  • a mixture of Trigonox 101 and acetonitrile may be provided to vessel 8 from vessel 3 and copolymerization can include providing the monomer PFP to vessel 8 from vessel 2 and the additional monomer provided from vessel 4 to vessel 8 can be 1 ,1 ,1-trifluoropropene (TFP).
  • a mole ratio of PFP/TFP provided to vessel 8 can be from about 1/1 to about 4/1.
  • Vessel 8 can then be heated to about 13O 0 C.
  • a composition that includes monomer units of PFP and TFP can be acquired that includes a mole ratio of monomer units of PFP to TFP of from about 1/2 to about 1/10.
  • an additional monomer may be added to vessel 8 from vessel 6.
  • This monomer can be added to vessel 8 in addition to the monomer added to vessel 8 from vessels 2 and 4.
  • the monomer VDF may be added to vessel 8 in addition to the monomers PFP and TFP added from vessels 2 and 4 respectively.
  • the mole ratios of PFP/VDF/TFP can be from about 1/1/1 to about 5/3/2.
  • a composition comprising monomer units of PFP, TFP 1 and VDF can be recovered.
  • the composition can include a mole ratio of PFP/VDF/TFP monomer units of from about 1/3/4 to about 1/8/11.
  • a mixture of Trigonox 101 and acetonitrile may be provided to vessel 8 from vessel 3 and copolymerization can include providing the monomer PFP to vessel 8 from vessel 2 and the additional monomer provided from vessel 4 to vessel 8 can be chlorotrifluoroethylene (CTFE).
  • CTFE chlorotrifluoroethylene
  • a mole ratio of PFP/CTFE provided to vessel 8 can be from about 2/1 to about 7/3. Vessel 8 can then be heated to about 130 0 C. Upon workup of a reaction mixture, a composition that includes monomer units of PFP and CTFE can be acquired that includes a mole ratio of monomer units of PFP/CTFE of from about 1/10 to about 1/66.
  • an additional monomer may be added to vessel 8 from vessel 6.
  • This monomer can be added to vessel 8 in addition to the monomer added to vessel 8 from vessels 2 and 4.
  • the monomer VDF may be added to vessel 8 in addition to the monomers PFP and CTFE added from vessels 2 and 4 respectively.
  • the mole ratios of PFP/CTFE/VDF can be from about 2.5/1/1.5 to about 10/2/3.
  • a composition comprising monomer units of PFP, CTFE, and VDF can be recovered.
  • the composition can include a mole ratio of PFP/CTFE/VDF monomer units of from about 1/4/5 to about 1/66/75.
  • the additional monomer provided from vessel 6 can be 3-isopropenyl- ⁇ , dimethylbenzylisocyanate (m- TMI).
  • m- TMI dimethylbenzylisocyanate
  • These reactants can be provided to Carius Tubes with the molar ratio of PFP/CTFE/m-TMi being at least about 2/1/1.
  • a composition including a mole ratio of PFP/CTFE/m-TMi monomer units can be recovered with the composition having a mole ratio of monomer units from about 3/6/1 to about 7/12/1.
  • the additional monomer provided from vessel 6 can be vinylene carbonate (VCA).
  • VCA vinylene carbonate
  • These reactants can be provided to Carius Tubes with the molar ratio of PFP/CTFE/VCA being from about 3/1/1 to about 5/4/1.
  • a composition including a mole ratio of PFP/ CTFE/VCA monomer units can be recovered with the composition having a mole ratio of monomer units of from about 1/5/4 to about 2/10/10.
  • the additional monomer provided from vessel 6 can be ethylene vinyl ether (EVE).
  • EVE ethylene vinyl ether
  • These reactants can be provided to Carius Tubes with the molar ratio of PFP/CTFE/EVE being from about 2/1/1 to about 6/3/3.
  • a composition including a mole ratio of PFP/CTFE/EVE monomer units can be recovered with the composition having a mole ratio of monomer units of from about 5/18/10 to about 1/80/19.
  • Figures 1 -48 are associated with the following non-limiting examples.
  • Example 1 Radical copolymerization of 2H-pentafluoropropene with Vinylidene fluoride(VDF)
  • a 160-mL Hastelloy (HC-276) autoclave reactor that can be equipped with inlet and outlet valves, a manometer, at least 5 mm Hg vacuum, and a rupture disc can be charged with 1.36 grams (4.7 x 10 "3 mole) of 2, 5-bis(tert- butylperoxy)-2,5-dimethylhexane (Trigonox 101) and 19 g of PFB, 25 grams (0.187 mole) of PFP and then 3.0 grams (4.7 x 10 '2 mole) of VDF.
  • the reactor can be progressively heated to 130 0 C.
  • the reactor temperature can be observed to increase 10 0 C and a pressure of the reactor to increase from 23 bars to 35 bars and descrease to 34 bars.
  • the reactor can then be placed in an ice bath for about 60 minutes and 16 grams of non-reacted VDF and PFP can be progressively released (the conversion of monomers can be about 32.1 wt %).
  • the reactor may then be opened and about 3 grams of what can be observed as a brown liquid can be obtained.
  • the PFB can be removed from the reactor, the sample can be dissolved in acetone, and precipitated by adding acetone solution into cold pentane.
  • the PFB can be removed from the reactor and the liquid precipitated from cold pentane and dried under vacuum (0.1 mm Hg at 40 0 C) to constant weight to obtain what can be observed as a viscous yellow oil. Yield: 37.1 wt. %.
  • Tg (by DSC) -22°C.
  • Trigonox 101 and 20 grams of PFB, 20 grams (0.15 mole) of PFP and 10 grams (6.67x1 O 2 mole) of HFP can be charged (69.4:30.6 mole % PFP:HFP).
  • the reactor can be progressively heated to 130 0 C. A temperature increase of about
  • Tg (by DSC) -46°C.
  • Tdec, 10 (by TGA): 110°C (in N 2 ); 95°C (in air).
  • the reactor can be heated to about
  • Tg (by DSC) -34°C.
  • Tdec, 10 (by TGA): 260 0 C (in N 2 ); 257°C (in air).
  • Trigonox 101 and 22 grams of PFB, 10 grams (7.6x10 2 mole) of PFP, 9 grams (14.1x10 "2 mole) of VDF, and 14.0 grams (9.3x10 '2 mole) of HFP can be charged (24.5/45.4/30.1 mole %, PFP/VDF/HFP).
  • the reactor can be progressively heated to 130 0 C. A temperature increase of about 10 0 C and a pressure increase of from about 28 bars to about 46 bars decreasing to about 26.3 bars can be observed.
  • About 4.0 grams of non-reacted PFP, VDF, and HFP can be removed from the reactor (the conversion of monomers can be about 80.5 wt. %) to yield about 50.8 grams of what can be observed as a brown liquid.
  • the PFB can be removed from the reactor and the liquid precipitated from cold pentane and dried under vacuum (0.1 mm Hg at 40 0 C) to obtain what can be observed as a yellow powder. Yield: 62.0 wt. %.
  • Tg(by DSC) -36°C.
  • Tdec, 10 (by TGA): 300 0 C (in N 2 ); 283°C (in air).
  • the terpolymer can be characterized by:
  • Tg (by DSC) -33°C.
  • Tdec io(by TGA): 317°C (in N 2 ); 314°C (in air).
  • Tg (by DSC) 4°C.
  • Tdec, 10 (by TGA): 156°C (in N 2 ); 150°C (in air).
  • Example 8 Radical copolymerizat ⁇ on of 2H-pentafluoropropene with TFMA
  • the copolymer can be characterized by:
  • PFB can be removed from the reactor and the liquid precipitated from cold pentane and dried under vacuum (0.1 mm Hg at 40 0 C) to constant weight to obtain what can be observed as a brown powder. Yield: 26.5 wt. %.
  • Tg (by DSC) 52°C.
  • Tdec, 10 (by TGA): 198°C (in N 2 ); 195°C (in air).
  • Example 10 Radical terpolymerization of 2H-pentafluoropropene with vinylidene fluoride and TFMA
  • the terpolymer can be characterized by:
  • Tg (by DSC) 53°C.
  • Tdec, 10 (by TGA): 208 0 C (in N 2 ); 202 0 C (in air).
  • Example 11 Radical terpolymerization of 2H-pentafluoropropene with vinylidene fluoride and TFMA
  • Tdec, 10 (by TGA): 239°C (in N 2 ); 236°C (in air).
  • Example 12 Radical terpolymerization of 2H-pentafluoropropene with vinylidene fluoride and TFMA
  • the reactor can be heated to about 130 0 C.
  • About 31.7 grams of non-reacted PFP and VDF can be removed from the reactor (the conversion vs. PFP+VDF can be about 21 wt. %) to yield about 66 grams of what can be observed as a brown liquid.
  • the PFB can be removed from the reactor and the liquid can be precipitated from cold pentane and dried under vacuum (0.1 mm Hg at 40 0 C) to constant weight to obtain what can be observed as a yellow-brown grease.
  • Tg (by DSC) 43°C.
  • Tdec, i O (by TGA): 212°C ⁇ in N 2 ); 203 0 C (in air).
  • Example 13 Radical terpolymerization of 2H-pentafluoropropene with vinyl idene fluoride and TFMA
  • Tg (by DSC) 48°C.
  • Tdec, 10 (by TGA): 263°C (in N 2 ); 262°C (in air).
  • Example 14 Radical terpolymerization of 2H-pentafluoropropene with vinylidene fluoride and TFMA
  • Tg (by DSC) -56°C.
  • Tdec, 10 (by TGA): 119°C (in N 2 ); 117°C (in air).
  • Tg (by DSC) -42°C.
  • Tdec, 10 (by TGA): 255°C (in N 2 ); 252°C (in air).
  • Example 17 Radical copolymerization of 2H-pentafluoropropene with 3, 3, 3-trifluoropropene (TFP)
  • Tdec, 10 (by TGA): 126°C (in N 2 ); 121 0 C (in air).
  • Example 18 Radical terpolymerization of 2H-pentafluoropropene with VDF and 3, 3, 3-trifluoropropene (TFP)
  • Tg (by DSC) -28°C.
  • Tdec, 10 (by TGA): 280 0 C (in N 2 ); 273°C (in air).
  • CTFE chlorotrifluoroethylene
  • Tg(by DSC) 8.0 0 C.
  • Tdec, 10 (by TGA): 282 0 C (in N 2 ); 271 0 C (in air).
  • Example 21 Radical terpolymerization of 2H-pentafluoropropene with CTFE and 3-isopropenyl- ⁇ , dimethylbenzylisocyanate (m-TMI)
  • Tg(by DSC) -35°C.
  • Tdec, 10 ( by TGA) :197°C (in N 2 ); 193°C (in air).
  • Example 22 Radical terpolymerization of 2H-pentafluoropropene with CTFE and Vinylene Carbonate (VCA)
  • Tg (by DSC) 49 0 C.
  • Tdec, K (by TGA): 313°C (in N 2 ); 312°C (in air).
  • Tdec, 10 (by TGA): 323°C (in N 2 ); 308 0 C (in air).
  • the halogenated compositions can be used alone and/or in combination with and/or incorporated with other compounds and used for the treatment and/or construction of paper materials, for example.
  • the compositions and derivatives can also be used to prepare polymeric solutions.
  • Polymeric solutions can be prepared as an aqueous or non-aqueous solution and applied to substrates to be treated, such as paper plates.
  • compositions can include acrylics, for example, that can be applied to finished carpet or incorporated into the finished carpet fiber before it is woven into carpet.
  • the compositions can be applied to carpet by a normal textile finishing process known as padding, in which the carpet is passed through a bath containing the composition or its derivative and, for example, latex, water, and/or other additives such as non-rewetting surfaces. The carpet can then be passed through nip rollers to control the rate of the add-on before being dried in a tenter frame.
  • Compositions and their derivatives can be used to treat substrates including hard surfaces such as construction materials such as brick, stone, wood, concrete, ceramics, tile, glass, stucco, gypsum, drywall, particle board, and chipboard. These compositions and mixtures can be used alone or in combination with penetration assistance compounds such as non-ionic
  • compositions can be applied to the surface of calcitic and/or siliceous architectural construction materials by known methods, for example, by soaking, impregnation, emersion, brushing, rolling, or spraying.
  • the compositions can be applied to the surface to be protected by spraying. Suitable spraying equipment is commercially available. Spraying with a compressed air sprayer is an exemplary method of application to the particular substrate.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des procédés de production utilisant du 1,1,3,3,3-pentafluoropropène (PFP) avec différents monomères fluorés et non fluorés. Les procédés de production chimiques peuvent inclure l'exposition d'un monomère de PFP à un ou plusieurs monomères de CTFE, HFP, TFP, et TFMA en vue de former une composition contenant au moins une unité monomère de PFP et une ou plusieurs des unités monomères de CTFE1, HFP, TFP, et TFMA. L'invention concerne également des compositions contenant au moins une unité monomère de PFP et une ou plusieurs unités monomères de CTFE, HFP, TFP, et TFMA.
PCT/US2007/017350 2006-08-03 2007-08-03 Compositions et procédés de production chimiques WO2008019068A2 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5719245A (en) * 1994-02-08 1998-02-17 Nippon Mektron, Limited Fluorine-containing copolymer and composition containing the same
WO2002044263A1 (fr) * 2000-12-01 2002-06-06 Dupont Dow Elastomers L.L.C. Composition fluoroelastomere presentant une aptitude excellente au traitement et des proprietes de faible temperature

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5719245A (en) * 1994-02-08 1998-02-17 Nippon Mektron, Limited Fluorine-containing copolymer and composition containing the same
WO2002044263A1 (fr) * 2000-12-01 2002-06-06 Dupont Dow Elastomers L.L.C. Composition fluoroelastomere presentant une aptitude excellente au traitement et des proprietes de faible temperature

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