Low molecular weight ternary copolymers vinylidenefluoride, curable at a low temperature, as the basis thermoinactivation sealants and protective coatings and method of production thereof

 

(57) Abstract:

Usage: as the basis thermoinactivation sealants and protective coatings of cold hardening, able to be applied in the absence or at low solvent content. Essence: low molecular weight ternary copolymers (CPF) vinylidenefluoride have the General formula:

< / BR>
where RF=-CF3,-OCF3,

< / BR>
l = 15-120, m = 3,5-32,5, n = 1,7-3,9, And== or Br, x = 1-3, AB, and if B=Br-; molecular weight equal SPL 2500-15000. The method of obtaining the CPF General formula (1) is obtained by copolymerization of vinylidenefluoride and comonomers in solution 1,2,2-Cryptor-1,1,2-trichloroethane in the presence of initiator - peralkylated General formula: where x = 1-3. As one of the comonomers used perfluoroalkyl vinyl ether with ester functional group. The process is carried out at a molar ratio of peralkylated to the sum of the monomers (is 0.0002-0,038): 1. It is possible to carry out the process in the presence of 1,2-dibromotetrafluoroethane at a molar ratio to the amount of comonomers (0,2-2,2): 1. Received the CPF otverzhdajutsja di - or polyamines at room temperature. 2 S. and 1 C.p. f-crystals, 1 table.

The present invention relates to the field of polucheniya General formula:

< / BR>
where RF-CF3, -OCF3, -OC3F7;

< / BR>
l 15-120; m a 3.5-32.5; n 1,7-3,9;

or Br-, x 1-3

,

with srednekamennogo molecular weight 2500-150000.

Such a plastic copolymers can be used in various technical fields, for example in the chemical, aviation industry, in the automotive industry, as the basis thermoinactivation sealants and protective coatings of cold hardening, able to be applied in the absence or at low solvent content.

It should be noted that the problem of obtaining thermoinactivation of cold-curing sealants used in the absence of solvent, is very important. This is because the use of solvent which must be removed from the sealant, creates certain difficulties, in particular, leads to a spatial change of the sealant, for example, shrinkage, distortion, voids. This difficulty is further increased, when to require elevated curing temperature.

Known copolymers containing units of vinylidenefluoride (EOF), hexaferrite (HFP) and perfluoroalkyl vinyl ether of the formula:

CF2CFO(CF2)nC(O)Ature 50oWith using as initiator ammonium persulfate at a molar ratio of monomers 1:0,77:0,2, respectively (1). However, these compounds are high molecular weight, i.e., solid products at room temperature, which does not allow to use them as the basis of a cold-curing sealants.

Known low molecular weight copolymers EOF and HFP containing in the polymer chain links EOF and HFP in a ratio of from 70:30 to 45:55, respectively, with molecular weight 1000-22000, having a form from viscous oils to greases at room temperature. The copolymers obtained in the mass at a temperature (100-250)oWith its own pressure in the presence of an initiator, such as benzoyl peroxide, dicumylperoxide or acetylpyrazine and transfer agent chain saturated, nestorgames acyclic halogen compounds, for example, methanol, acetone, ethyl acetate, at a molar ratio of agent chain transfer to the sum of the monomers of from 0.025 to 1.2 (2). Such copolymers intended for use as plasticizers fluorocarbon elastomers to improve their processing and devulcanized with them (such as hexamethylenediisocyanate) at temperatures Watamu cannot be used for sealants and coatings of cold hardening.

The closest analogue on purpose are liquid at room temperature iodine-containing copolymers EOF obtained by copolymerization EOF more than one monomer selected from the group of HEXAFLUOROPROPYLENE, tetrafluoroethylene, performatively ether or performatively ether, in the presence of a source of radicals, such as polyformaldehyde and iodine floralina RFJxwhere TF- perfluorocarbon radical, at a molar ratio of iodine to the sum of the monomers from 0,0008 to 0.1. The process is carried out at temperatures from -20oWith up to 150oC. For copolymerization may be used any method: emulsion or solution polymerization. As a solvent used chlorofluorocarbons, for example, 1,1,2,2-titrator-1,2-dichloroethane; 1,1,2-Cryptor-1,2,2-trichloroethane and other (3).

This method is the closest analogue of the method of producing low molecular weight copolymers EOF according to the invention. Obtained in accordance with the patent compounds are legallywhere persepolitan, preferably containing 40-80 mol. VFI 2-20 wt. limit of iodine with a molecular mass of 900-10000. As the vulcanizing agent can be used, for example, organic is whether coverings, however, as indicated in the patent examples, the curing process takes place at 100oWith that it is not possible to use them as the basis sealants and coatings, cured at ambient temperature. Described in the patent is a method of obtaining low molecular weight copolymers EOF has also the following disadvantages: low yield of copolymer and lengthy process. Thus, in the above example copolymerization EOF and HFP (molar ratio 1:1,2) when 23oWith using as a source of radicals - bis-(trichloroethanol)peroxide in the solution of trichlorotrifluoroethane, and as the iodine-containing floralina 1,4-itperformance taken in a molar ratio to the sum of monomers 0,000046:0,0048:1, respectively, during the trial, 67 h, and the yield of copolymer 10 wt.

An object of the invention is to obtain a low molecular weight ternary copolymers EOF having fluidity at temperatures of 0-50oWith on the basis of which the absence or at low solvent content can be received sealants and coatings of cold hardening, which have satisfactory initial physical-mechanical properties of the P> This goal is achieved by the synthesis of copolymers of the General formula (1).

The copolymers produced by interaction EOF with a monomer selected from the group: HFP, performatively ether (PPPSA), performability ether (PVPVE), and the third monomer performancelevel ether with ester functional group (PFVS). As the latter can be used for the connection:

CF2CFO(CF2)3C(O)OCH3(PFWE-I)

CF2CFO(CF2)5C(O)OCH3(PFWE-II)

CF2(CF2)3OCF(CF3)C(O) CH3(PFWE-III)

The process is carried out in the presence of initiator - bis-(perftorpolietilena)peroxide of the formula (2)

< / BR>
where x is 1-3,

in a solution of 1,1,2-Cryptor-1,2,2-trichloroethane (halon-113) at a temperature of 25-40oC. the Molar ratio of EOF, the second monomer, is PFWA 1: (0,5-0,6): (0,03-0,1), respectively, and the molar ratio of peroxide to the sum of the monomers equal to (is 0.0002-0,038):1.

With the aim of obtaining copolymers with improved resistance to certain corrosive environments, for example, gaseous fluorine, the process is carried out in the presence of 1,2-dibromotetrafluoroethane, which is used in a molar ratio to the sum of monomers equal to (0,2-2,2):1.

Alenia within 4-6 hours Removing the solvent on a rotary evaporator to produce a copolymer with a yield of 70-90 wt.

Used as comonomers olefins and other products used are available products and are produced in accordance with the following standards:

EOF THE 6-027647-77

THE SPC THAT 95,417-77

PFMPE THE 6-021866-85

PVPVE THE 38.403577-88

Refrigerant-113 GOST 23844-79

1,2-dibromotetrafluoroethane GOST 15899-79

Used as an initiator bis(perftorpolietilena)-peroxide get a way similar to that described (Z. S. Sibert, D. Swern. Analyt. Chem, 30, N 3, 385 (1958)), and which consists in the interaction of the relevant foramerican with hydrogen peroxide in the presence of potassium hydroxide at a temperature of -10oWith the solution halon 113.

Removed after separation of the target product, the solvent and 1,2-dibromotetrafluoroethane can be re-used in copolymerization processes.

Srednekamennogo molecular weight determined ebullioscopic, dissolving a portion of the copolymer in pentafluorobenzene. Dynamic viscosity of the copolymer measured by a viscometer of Galera.

The composition and structure of the obtained copolymers was determined by elemental analysis and NMR1 is th use solutions sopolimerov hexaferrite. The following examples illustrate the invention.

Example 1.

In vakuumirovaniya and cooled machine stainless steel with a capacity of 0.5 liters, equipped with a motor with shielded drive, mechanical propeller stirrer, manovacuummeter, the two fittings for the supply of reagents and a jacket for temperature control, load of 37.6 g (0.59 mol) EOF, 51.8 g (0,345 mol) HFP, 19,0 g (0,047 mol) PFVA-P, 110 ml (0,037 mol) 0.34 M solution of bis-(perftorpolietilena)peroxide formula 2 (where x (1) halon 113 and an additional 234 g of HFC-113. The molar ratio EOF:HFP: PFWE-P is 1: 0, 59:0-079, respectively, and the molar ratio of peroxide to the sum of the monomers is 0,038:1.

The polymerization is carried out at a temperature of 40oC. the Initial pressure 0.7 MPa, for five hours falls to 0.18 MPa. After the fall of the pressure of the reaction mass is stirred at 40oEven within hours, and then discharged into the flask of a rotary evaporator and vacuum (3-4 mm RT.CT.) distilled off the solvent and volatile products, gradually warming the contents of the flask to 150oC. Then the copolymer is heated in vacuum for hours at 150-160oC. Unload 98 g plastic copolymer (yield 91 wt. it is ASS="ptx2">

According to NMR data19F-spectroscopy the structure of the obtained copolymer corresponds to the formula 1, and the molar ratio of chain fragments (EOF) (GUF) (PPVE-P) (0.32 4,40 0,34 respectively. Taking into account the molecular weight of the copolymer indices l, m, n in formula 1 is equal to: l 27,3, 6,2 m, n 2,1 and leaf fragments And presented by the group in the amount of 1.98.

For the copolymer of formula 1 having the above index values calculated elemental composition, wt. [C] 29,9;[F] 65,4; [H] 1,49, and for samples of the obtained copolymer with the method of elemental analysis found, wt. [C] 30,3; [F] 65,2; [H] 1,4.

Example 2.

In the conditions of example 1 are copolymerization of 40.8 g (0.64 mol) EOF, 57.4 g (0.38 mol) HFP and 6.25 g (0.02 mol) of PPVE-1 in the presence of 31.8 ml (0,0073 mol) of 0.23 M solution of bis-(perftorpolietilena)peroxide formula 2 (where x 3) halon-113 and additionally 386 g of HFC-113. The molar ratio EOF HFP, PPVE-1 is 1:0,60:to 0.032, respectively, and the molar ratio of peroxide to the sum of the monomers is 0,007:1. The process is carried out at 30oWith over four hours and produce 80 g of the copolymer (output mos. ) with 15000.

According to NMR data19F-spectroscopy the structure of the obtained copolymer corresponds to the formula 1, and the mole who assy copolymer indices l, m, n in formula 1 is equal to l 120,7; m 32,5; n 3,9, and leaf fragments A,B presents the group in the amount of 1.85.

For the copolymer of formula 1,0 having the above index values calculated elemental composition, wt. [C] 31,0; [F] 65,4; [H] 1,69, and the obtained copolymer with the method of elemental analysis found, wt. [C] 31,1; [F] 65,9; [H] 1,6.

Example 3.

In contrast to the examples of N 1 and N 2 the copolymerization is carried out in the presence of dibromotetrafluoroethane.

In vakuumirovaniya and cooled machine stainless steel with a capacity of 0.5 liters, equipped with a motor with shielded drive, mechanical propeller stirrer, jacketed for temperature control, load of 40.4 g (0,63 mol) EOF 56,6 g (0.38 mol) of the GUF, 10.8 g (0.035 mol) of PPVE-1, 44,8 ml (0,016 mol) 0,355 M solution of bis-(perftorpolietilena)-peroxide formula 2 (where x 2) halon-113, 59.8 g (0.23 mol) of 1,2-dibromotetrafluoroethane and additionally 341 g of HFC-113. The molar ratio EOF:HFP:PPVE-1 is 1:0,60:0,056, respectively, and the molar ratio of peroxide to the sum of the monomers is of 0.015: 1, and the molar ratio of dibromotetrafluoroethane to the sum of the monomers is of 0.015: 1, and the molar ratio of dibromotetrafluoroethane to the sum of the monomers 0,22:1.

The polymerization is carried out at plants the pressure of the reaction mass is stirred at 40oEven within one hour, and then discharged into the flask of a rotary evaporator and vacuum (3-5 mm RT.CT.) distilled off the solvent and volatile products, gradually heating the contents of the flask to 150oC. the polymer was Then heated in vacuum for one hour at 150-160oC. Unload 83 g of viscous flow of the polymer (exit 77 wt. ) having a dynamic viscosity () if 50oWith equal 62 Pass and srednekamennogo molecular weight equal to 5500. According to NMR data19F-spectroscopy the structure of the copolymer corresponds to the formula 1, the molar ratio of chain fragments (EOF): (HFP): (PPVE-1) is 0.09:3,32:1:0.25 in. Elemental analysis of bromine found in the composition of the copolymer 1.5 wt. Br. Taking into account the molecular weight of the copolymer indices l, m, n in formula 1 is equal to: l 37,2; 11,2 m; n is 2.8, and leaf fragments a, b are two types: the number of 1.01 and Br -0 in the number of 1.03. For the copolymer of formula 1, having the values of the indices calculated elemental composition, wt. [C] 29,8; [F] 64,2; [H] 1,50, and for samples of the obtained copolymer with the method of elemental analysis found, wt. [C] 29,2; [F] 64,3; [H] 1,6=

Example 4.

In the conditions of example No. 3 carry out the copolymerization of 38.7 g (of 0.60 mol) EOF, a 94.6 g (0.36 mol) of PVPVE and 14.7 g (0,048 mol) PPVE-1 in the presence and 48.8 ml (0.015 mol) 0,31 M p is ethane and optionally 248 g of HFC-113. The molar ratio EOF:PVPVE:PPVE-1 is 1: 0,59:0,079, respectively; the molar ratio of peroxide to the sum of the monomers is of 0.015:1, and the molar ratio of 1,2-dibromotetrafluoroethane to the sum of the monomers 0,22:1. The process is carried out at 40oWith over four hours and emit 120 g of the copolymer (output mos. ), with

According to NMR data19F-spectroscopy the structure of the copolymer corresponds to the formula 1, and the ratio of chain fragments (EOF) (PVPVE) (PPVE-1) is 0.06:2,33:1:0,13, respectively. Elemental analysis of bromine found in the composition of the copolymer by weight 0.9. Br. Taking into account the molecular weight of the copolymer indices l, m, n in formula 1 is equal to: l 40,9; m 17,5; n, 2,3 - and leaf fragments a, b are two types: in the amount of 1.05 and Br in the number of 0,94.

For the copolymer of formula 1, having the values of the indices calculated elemental composition, wt. [C] 27,4; [F] 65,8; [H] of 1.05, for samples obtained copolymer with the method of elemental analysis found, wt. [C] 27.9; [F] 65,3; [H] 1,2.

Example 5.

In the conditions of example No. 3 carry out the copolymerization of 42.8 g (0.67 mol) EOF, to 59.4 g (0.40 mol) HFP and 17.5 g (0,043 mol of PFVA-P in the presence of 23.4 ml (0,008 mol) 0,355 M solution of bis-(perftorpolietilena)peroxide formula 2 (where x=1) halon-113, 203 g (0,78 mol, respectively; the molar ratio of peroxide to the sum of the monomers is 0,0075: 1 and the molar ratio of 1,2-dibromotetrafluoroethane to the sum of the monomers of 0.7:1. The process is carried out at 25oWith over six hours and allocate 89 g of the copolymer (exit 77 wt. ), with

According to NMR data19F-spectroscopy the structure of the copolymer corresponds to the formula 1, and the ratio of chain fragments (EOF):(PFWE-P) is 0,07:3,28:1:0,32, respectively. Elemental analysis of bromine found in the composition of the copolymer by weight 2.5. Br. Taking into account the molecular weight of the copolymer indices l, m, n in formula 1 is equal to: l 27,8; 8,5 m; n 2.7, leaf fragments a, b are two types: the number of 0.59 and Br in the number of 1.40.

For the copolymer of formula 1, having the values of the indices calculated elemental composition, wt. [C] 29,3; [F] 63,7; [H] is 1.42, and for samples of the obtained copolymer with the method of elemental analysis found, wt. [C] 29,8 [F] 64,0; [H] 1,5.

Example 6.

In the conditions of example No. 3 carry out the copolymerization 40,1 g (0,63 mol) EOF, 55.8 g (of 0.37 mol) HFP and 25.4 g (to 0.060 mol) PFVA-sh in the presence of 21.2 ml (0,008 mol) 0,375 M solution of bis-(perftorpolietilena)peroxide formula 2 (where x=1) halon-113 and 401 g (1.54 mol) of 1,2-dibromotetrafluoroethane. The molar ratio of EOF:HFP:PFWE-W with the ratio of peroxide to the sum of the monomers of 1.46:1. The process is carried out at 25oWith over six hours and unload 90 g of a copolymer (yield 74 wt.), having

According to NMR data19F-spectroscopy the structure of the copolymer corresponds to the formula 1, and the ratio of chain fragments (EOF) (GUF) (PPVE-W) is 0.06: 4,30:1:0,50, respectively. Elemental analysis of bromine found in the composition of the copolymer of 5.6 wt. Br. Taking into account the molecular weight of the copolymer indices l, m, n in formula 1 is equal to: l 15,0; 3,5 m; n of 1.7, and leaf fragments a, b are two types: the number of 0.21 and Br in the amount of 1.75.

For the copolymer of formula 1, having the values of the indices calculated elemental composition, wt. [C] 28,2; [F] 60,2; [H] 1,40, for samples obtained copolymer with the method of elemental analysis found, wt. [C] 28,5; [F] 60,1; [H] 1,4.

Example 7.

In the conditions of example No. 3 carry out the copolymerization of 40.8 g (0.64 mol) EOF, to 53.0 g (0.32 mol) of PFMPE and 14.6 g (0,048 mol) PPVE-1 in the presence of 13.8 ml (0.002 mol)0,145 M solution of bis-(perftorpolietilena)peroxide formula 2 (where x1) halon-113 and 580 g (2,23 mole) of 1,2-dibromotetrafluoroethane. The molar ratio EOF:PFMPE:PPVE-1 is 1:0,50:0,075, respectively; the molar ratio of peroxide to the sum of the monomers is is 0.0002:1 and the molar ratio of 1,2-dibromotetrafluoroethane the course of 71 wt.), having

According to NMR data19F-spectroscopy the structure of the copolymer corresponds to the formula 1, and the ratio of chain fragments (EOF):(PPPSA):(PPVE-1) is 2,66: 1: 0,14, respectively. Fragments of end groups corresponding to the structure using NMR19F-spectroscopy is not detected. Elemental analysis of bromine found in the composition of the copolymer of 3.3 wt. Br. Taking into account the molecular weight of the copolymer indices l, m, n in formula 1 is equal to: l 31,9; m 12,6; n 1,7, and leaf fragments And presents one type of Br in the number of 1.98.

For the copolymer of formula 1, having the values of the indices calculated elemental composition, wt. [C] 28,4; [F] 61,2; [H] 1.43 and for samples of the obtained copolymer with the method of elemental analysis found, wt. [C] 29,2; [F] 61,0; [H] 1,5.

The copolymers obtained in examples 1, 3, 5-7 represent the viscous flow of the translucent liquid at room temperature, and the copolymers obtained in examples 2, 4 have the form of greases at room temperature and have fluidity at the 50oC.

All the obtained copolymers otverzhdajutsja aliphatic or fatty-aromatic di - and polyamines at room temperature, using 3-8 wt.h. hardener per 100 wt.h. copolym the minutes. The composition is placed in the mold and kept in a press under a pressure of 10 MPa at room temperature for 18-24 hours the resulting vulcanizates are rubber-like materials, getting the maximum physical-mechanical properties through 120-170 hours at room temperature or by brief heating at 70oC. In compositions based on copolymers of 2, 4 advanced use 10-20 wt.h. solvent, for example ethyl acetate.

The results of physico-mechanical testing hardened compositions on the basis of the obtained copolymers containing as a hardener 4-7 wt.h. xylylenediamine (KDA, mixture of isomers: m:p 75:25) are shown in table 1. From the data presented in table 1, it follows that already for 24 h at room temperature can be obtained vulcanizates with technologically acceptable properties. It should be noted that the copolymers obtained in the presence of 1,2-dibromotetrafluoroethane (examples 3-7), along with the above properties, increased resistance to such aggressive environments, as gaseous F2. So comparative testing of samples of vulcanizates obtained on the basis of copolymer 1 and 5, treated with gaseous fluorine for 120 h at 20oWith Et all copolymers according to the invention is dried at room temperature allows their use as polymer base thermoinactivation sealants and protective coatings, used in the absence of or at low solvent content. The compositions can additionally be entered the number of necessary technological additives (adhesives, thinners, retarders, fillers, anti-corrosion additives and others).

The method of obtaining low molecular weight copolymers EOF according to the invention is simple in technological performance, does not require a large investment of time, allows to produce target products with a unique combination of properties, high yield.

1. Low molecular weight ternary copolymers vinylidenefluoride General formula

< / BR>
where RF-CF3, -OCF3, -OC3F7;

-(CF2)3C(O)OCH3, -(CF2)5C(O)OCH3, -(CF2)3OCF(CF3)C(O)OCH3;

l 15 120;

m 3,5 32,5;

n 1,7 3,9;

or Br-,

x 1 3; AB and if it is B Br-,

with srednekamennogo mol.m. 2500 15000, curable at a low temperature, as the basis thermoinactivation sealants and protective coatings.

2. The method of obtaining low molecular weight ternary copolymers vinylidenefluoride and comonomers in solution 1,2,2-Cryptor-1,1,2-trichloroethane in the presence of initiator peralkylated, otlichayushiesya group, as an initiator - peralkylated General formula:

< / BR>
where x 1 3,

and the process is carried out at a molar ratio of peralkylated to the sum of the monomers (is 0.0002 0,038) 1.

3. The method according to p. 2, characterized in that the process is carried out in the presence of 1,2-dibromotetrafluoroethane when the molar ratio of 1,2-dibromotetrafluoroethane to the sum of the comonomers (0,2 2,2) 1.

 

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16 ex, 3 tbl

FIELD: electricity.

SUBSTANCE: gel polymer electrolyte includes polymer matrix obtained by means of interaction by grafting to copolymer of trifluorchloroethylene and vinylidene fluoride of copolymer of polyethylene glycol acrylate in organic solvent, at content of polyethylene glycol acrylate of 20-75%, where in grafted copolymer the content of links of vinylidene fluoride is 25-35%, with further introduction of lithium salt in amount of 5 to 20% in terms of 100 weight parts of matrix.

EFFECT: obtaining gel polymer electrolyte with high mechanical strength, stable structure of polymer and increased ionic conductivity; lithium current source has improved electric and operating characteristics.

2 cl, 1 tbl

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