CN113801625B - Hybrid polythioether sealant - Google Patents
Hybrid polythioether sealant Download PDFInfo
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- CN113801625B CN113801625B CN202111259347.4A CN202111259347A CN113801625B CN 113801625 B CN113801625 B CN 113801625B CN 202111259347 A CN202111259347 A CN 202111259347A CN 113801625 B CN113801625 B CN 113801625B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/02—Polythioethers; Polythioether-ethers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
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Abstract
The invention belongs to the technical field of high polymer material sealants, and relates to synthesis of liquid hybrid polythioether rubber with long-term high temperature aging resistance and good low-temperature performance and application of the liquid hybrid polythioether rubber in a sealant. The bifunctional hybrid polythioether rubber is generated by reacting a dimercapto-terminated compound with a diolefin-terminated phenylene compound in the presence of free radicals; the tetrafunctional degree hybrid polythioether rubber is polymerized by micromolecular polythioether rubber and tetraolefin-terminated fluorosilicone polymer in the presence of free radicals, the tetrafunctional degree hybrid polythioether rubber is used as raw rubber matched filler, a coupling agent is used, manganese dioxide is used as a vulcanizing agent to prepare a sealant, and the sealant after vulcanization has good high-temperature aging resistance, oil resistance and low-temperature resistance and can be used for sealing an aircraft fuel tank.
Description
Technical Field
The invention belongs to the technical field of high polymer material sealants, and relates to synthesis of liquid polythioether rubber with long-term high-temperature aging resistance and good low-temperature performance and a method for preparing a sealant by using the liquid polythioether rubber as a raw material.
Background
The liquid polythioether rubber has good oil resistance because the molecules contain elements such as oxygen, sulfur and the like with larger polarity, and the sealant prepared by using the liquid polythioether rubber is widely applied in the field of aviation. US5912319 discloses a highly efficient method for synthesizing polythioethers by addition polymerization of divinyl compounds and dithiol compounds in the presence of free radicals to form polymeric materials, which is very simple and highly productive, and requires substantially no subsequent treatment, and is a currently highly efficient method for synthesizing polythioethers. However, the molecular chains of these liquid polythioether rubbers mainly contain C-C, C-O, C-S and other bonds, and these molecular bonds are easy to undergo thermo-oxidative aging in hot air, resulting in molecular chain scission, and thus long-term use at high temperature cannot be realized, for example, after a sealant prepared from the polythioether rubber is subjected to thermo-oxidative aging at 120 ℃ for 500 hours, the elongation at break is only less than 50%. In order to improve the aging resistance of the material, many similar methods are disclosed, for example, epoxy resin or polyurethane resin is used for modifying the material, and a large number of rigid chain segments are added in a molecular chain, but the modification method can lose the low-temperature performance of the polythioether rubber and reduce the temperature flexibility, and meanwhile, due to the introduction of a large number of C-C bonds, the oil resistance of the polythioether rubber is influenced to a certain extent, the application range is narrowed, and the sealing requirements of long-term high-temperature aging resistance and better low-temperature performance are difficult to meet.
Disclosure of Invention
The purpose of the invention is: provides a synthesis method of hybrid liquid polythioether rubber with long-term high-temperature aging resistance and better low-temperature performance and application of the hybrid liquid polythioether rubber in preparation of polythioether sealant.
The technical scheme of the invention is as follows:
a long-term high-temperature aging resistant hybrid polythioether sealant consists of a component A base paste and a component B vulcanizing paste, wherein the component A is the base paste, and the component B is the vulcanizing paste;
the component A consists of bifunctional hybrid polythioether rubber, tetrafunctional hybrid polythioether rubber, a filler, a coupling agent and a plasticizer;
the tetrafunctional hybrid polythioether rubber accounts for 2 to 8 percent of the weight of the component A, can improve the crosslinking degree and the mechanical strength of a system, and the filler accounts for 5 to 30 percent of the weight of the component A; the plasticizer accounts for 1 to 5 percent of the weight of the component A; the coupling agent accounts for 0.5 to 2 percent of the weight of the component A, is a perfluoro silane coupling agent, has better compatibility with the generated sealant, and can improve the bonding property of the sealant;
the balance being difunctional hybrid polythioether rubber.
The bifunctional hybrid polythioether rubber can be represented by the formula (I):
wherein R is 1 Can be represented by formula (II):
-[(-CH 2 -) a -O-] b -(CH 2 ) c -Ⅱ
a is 2 to 6; b is 1 to 6; c is 2-8 and is a flexible chain segment, so that the flexibility of the whole polymer is ensured;
R 2 is H or F;
m＝1～3；
n is 3-10, the bifunctional hybrid polythioether rubber contains a phenylene structure, is a rigid chain end, and can obtain better heat resistance.
The synthesis method of the bifunctional hybrid polythioether rubber comprises the following steps: polymerizing a bis-mercapto-terminated compound with a diolefin-terminated phenylene compound in the presence of a free radical, wherein:
bis-mercapto-terminated compounds of the general formula: HS-R 1 -SH；
A diolefin-terminated phenylene Compound of formula (III):
the free radical initiation conditions of the two compounds are thermal initiation or photoinitiation, wherein the initiator used for thermal initiation can be azobisisobutyronitrile, azobisisovaleronitrile, azobisisoheptonitrile or peroxide, and the like, and the heating temperature is 60-90 ℃; the initiator used for the photo-initiation may be ultraviolet light, etc., and the initiator may be a conventional photoinitiator such as benzil ketals, acetophenones, benzophenones.
The above-mentioned tetrafunctional hybrid polythioether rubber can be represented by the formula (IV):
wherein x =1 to 5;
R 3 can be represented by formula (V):
-CH 2 CH 2 SR 1 S-[-CH 2 CH 2 O(CH 2 CH 2 O) y CH 2 CH 2 SR 1 -S-] z -HⅤ
y is 1 to 3;
z is 1 to 5.
The synthesis method of the tetrafunctional hybrid polythioether rubber comprises the following steps: polymerizing a fluorosilicone polymer terminated by micromolecular polythioether rubber and tetraolefin in the presence of free radicals, wherein:
the general formula of the micromolecular polythioether rubber is as follows: HS-R 1 S-[-CH 2 CH 2 O(CH 2 CH 2 O) y CH 2 CH 2 SR 1 -S-] z -H；
A tetraolefm-capped fluorosilicone polymer of the general formula (vi):
the fluorine-silicon structure contains fluorine, so that the polarity of the material is improved, better oil resistance can be ensured, and meanwhile, due to the existence of fluorine atoms, the attack of other free radicals can be shielded, and the fluorine-silicon structure has better aging resistance.
The free radical initiation conditions of the two chemical substances are thermal initiation or photoinitiation, wherein the initiator used for thermal initiation can be azobisisobutyronitrile, azobisisovaleronitrile, azobisisoheptonitrile or peroxide, and the heating temperature is 60-90 ℃; the initiator used for the photo-initiation may be ultraviolet light, etc., and the initiator may be a conventional photoinitiator such as benzil ketals, acetophenones, benzophenones.
The filler is one of fumed silica and precipitated silica or a mixture of a plurality of substances; the plasticizer is one or a mixture of phthalic acid substances, chlorinated paraffin or tributyl phosphate; the coupling agent is one or a mixture of more of perfluorosilane coupling agents, and comprises perfluoropropyl trimethoxy silane, perfluorooctyl triethoxy silane and heptadecafluorodecyl trimethoxy silane;
the component B consists of manganese dioxide, tributyl phosphate and an accelerant D; the manganese dioxide accounts for 30 to 60 percent of the weight of the component B; the accelerator D accounts for 0.5 to 5 percent of the weight of the component B; the balance of tributyl phosphate;
the component A and the component B are stored separately.
A method of sealing using the sealant described above, characterized by: mixing the component A and the component B before use, wherein the weight ratio of the component A to the component B is 100: 8-12, mixing the component A and the component B by adopting a manual mixing mode for 3-5 minutes; then sealing operation is carried out within 3 hours, sealant is coated on the sealed position, and the coating thickness is 2-10 mm; finally vulcanizing at room temperature for 3-7 days.
The invention has the advantages that: the synthesis method of the liquid polythioether rubber with long-term high-temperature aging resistance and good low-temperature performance is provided, and the polythioether rubber is prepared into the polythioether sealant, and has the following specific advantages:
1. the main chain of the synthesized bifunctional hybrid polythioether rubber contains benzene rings and C-Si bonds, so that the high-temperature resistance and the aging resistance of the polymer are improved, and meanwhile, the two ends of the rigid chain segment are provided with flexible chain segments, so that the flexibility of the whole polymer is ensured, and the strength and the heat resistance are ensured, and the bifunctional hybrid polythioether rubber has high elongation and low-temperature resistance. During synthesis, the catalyst is prepared by using a rapid reaction between olefin and mercaptan, the reaction can be rapidly reacted under free radicals, and the yield is high;
2. the synthesized tetrafunctional hybrid polythioether rubber has a main chain of Si-O bonds, and a middle silicon side group containing trifluoropropyl, so that the temperature resistance and the oil resistance are ensured. Meanwhile, the side group is micromolecule polythioether with four flexible long chains, the end is blocked by SH, and the micromolecule polythioether is used as a cross-linking agent in a sealing agent to enhance the cross-linking density of a sealing system.
3. The perfluorosilane coupling agent is added into the sealant and attached to the surface of the filler, so that a good shielding effect can be achieved, and the aging resistance and the oil resistance of the sealant can be improved in an auxiliary manner.
Detailed Description
Example 1: bifunctional hybrid polythioether rubber A1
168g of HSCH 2 CH 2 OCH 2 CH 2 SH and 280g of diolefin-terminated phenylene Compound (chemization)Chemical formula III, wherein R 2 To H, m = 1) was placed in a flask, 5g of azobisisoheptonitrile was added, heated to 70 ℃, and after 8 hours of reaction, a viscous sample A1 liquid at room temperature was obtained, which had a number average molecular weight of 3250 and a glass transition temperature of-45 ℃ by GPC molecular test.
Example 2: bifunctional hybrid polythioether rubber A2
200g of HSCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 SH and 360g of a diolefin-terminated phenylene Compound (formula III, where R 2 M = 1) was placed in a flask, 6g of azobisisobutyronitrile was added, the mixture was heated to 70 ℃, and after 8 hours of reaction, the reaction was stopped to obtain a viscous sample A2 which was liquid at room temperature and had a number average molecular weight of 3550 and a glass transition temperature of-43 ℃ as measured by GPC.
Example 3: bifunctional hybrid polythioether rubber A3
200g of HSCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 SH and 370g of a diolefin-terminated phenylene Compound (formula III, where R is 2 H, m = 2) was placed in a flask, 3g of photoinitiator α, α -dimethoxy- α -phenylacetophenone was added, irradiation was carried out for 30min under an ultraviolet lamp, the reaction was stopped to obtain a viscous sample A3 which was liquid at room temperature, the number average molecular weight was 3650 by GPC test, and the glass transition temperature was-50 ℃.
Example 4: tetrafunctional hybrid polythioether rubber B1
2800g of a small molecular weight polythioether rubber HS-CH with a number average molecular weight of 650 2 CH 2 OCH 2 CH 2 S-[-CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 SCH 2 CH 2 OCH 2 CH 2 -S-] z Placing 520g of diolefin end-capped fluorosilicone polymer (chemical formula VI, number average molecular weight 500) in a flask, heating 5g of azobisisobutyronitrile to 70 ℃, reacting for 8 hours to obtain a viscous sample B1 which is liquid at room temperature, wherein the viscosity is 8Pa.s, and the glass transition temperature is-58 ℃ through testing.
Example 5: tetrafunctional hybrid polythioether rubber B2
3360g of small molecular weight polythioether rubber HS-CH with the number average molecular weight of 800 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 S-[-CH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 SCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 -S-] z -H and 660g of a diolefin-terminated fluorosilicone polymer (chemical formula VI, number average molecular weight 650), 2g of a photoinitiator, alpha-dimethoxy-alpha-phenylacetophenone was added, and the mixture was irradiated under an ultraviolet lamp for 30min to obtain a viscous sample B2 which was liquid at room temperature and had a viscosity of 10Pa.s and a glass transition temperature of-59 ℃ as measured.
Example 6: the samples A1 and B1 were added with fillers and the like and mixed using a three-roll mill to form component a of the sealant, as shown in table 1, component B was a cured paste, and the weight ratio of component a to component B was 100:12 mixing to make a final sealant;
TABLE 1 formulation composition of sealant 1
Example 7: the samples A2 and B1 were added to a filler and mixed using a three-roll mill to form component a of the sealant, as shown in table 2, component B was a cured paste, and the weight ratio of component a to component B was 100:10 to produce the final sealant;
TABLE 2 formulation composition of encapsulant 2
Example 8: the samples A3 and B2 were added to a filler and mixed using a three-roll mill to form component a of the sealant, as shown in table 3, component B was a cured paste, and the weight ratio of component a to component B was 100:12 mixing to make a final sealant;
TABLE 3 formulation composition of encapsulant 3
Comparative example 9: mixing common polythioether rubber (number average molecular weight 3800, using HSCH) 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 SH and diethylene glycol divinyl ether synthesized under free radical conditions) were added with fillers and the like and mixed using a three-roll mill to form component a of the sealant, as shown in table 4, component B was a cured paste, and component a and component B were mixed in a weight ratio of 100:12 mixing to make a final sealant;
TABLE 4 formulation composition of encapsulant 4
Comparative example 10: mixing common polythioether rubber (number average molecular weight 3800, using HSCH) 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 SH and diethylene glycol divinyl ether synthesized under free radical conditions) were added with fillers and the like and mixed using a three-roll mill to form component a of the sealant, as shown in table 5, component B was a cured paste, and component a and component B were mixed in a weight ratio of 100:10 to produce the final sealant;
TABLE 5 formulation composition of encapsulant 5
The properties of the above 5 sealants after vulcanization were tested and the results are shown in table 6.
TABLE 6 Properties of polythioether sealants after vulcanization
From the table 6, the sealant prepared by the three synthesized liquid polythioether rubbers has good mechanical properties, and simultaneously, after the sealant is aged at 120 ℃ for 500 hours in hot air, the sealant still has good mechanical properties, and meets the sealing requirements that the tensile strength is more than or equal to 0.8MPa and the elongation at break is more than or equal to 75%, but the common polythioether cannot meet the requirements, so that the prepared polythioether sealant has more excellent heat-resistant aging performance, the obtained polythioether sealant has better medium-resistant performance, the volume expansion rate in 3# aviation kerosene is equivalent to that of the common polythioether sealant, and the sealant has better low-temperature flexibility at-55 ℃.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solutions of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive various equivalent modifications or substitutions within the technical scope of the present invention, and these modifications or substitutions should be covered within the scope of the present invention.
Claims (8)
1. A hybrid polythioether sealant characterized by: the adhesive consists of a component A base paste and a component B vulcanizing paste, wherein the mass ratio of the component A base paste to the component B vulcanizing paste is 100:8 to 12:
the component A consists of bifunctional hybrid polythioether rubber, tetrafunctional hybrid polythioether rubber, a filler, a coupling agent and a plasticizer;
the tetrafunctional hybrid polythioether rubber accounts for 2 to 8 percent of the weight of the component A, and has a fluorine silicon structure;
the filler accounts for 5 to 30 percent of the weight of the component A;
the plasticizer accounts for 1 to 5 percent of the weight of the component A;
the coupling agent accounts for 0.5 to 2 percent of the weight of the component A;
wherein the tetrafunctional hybrid polythioether rubber has a structure shown in a formula (IV):
wherein x =1 to 5;
R 3 can be represented by formula (V):
-CH 2 CH 2 SR 1 S-[-CH 2 CH 2 O(CH 2 CH 2 O) y CH 2 CH 2 SR 1 -S-] z -H Ⅴ
y is 1 to 3;
z is a number of 1 to 5,
the balance is bifunctional hybrid polythioether rubber which has a silicon-containing phenylene structure,
the component B consists of manganese dioxide, tributyl phosphate and an accelerant D;
the manganese dioxide accounts for 30 to 60 percent of the weight of the component B;
the accelerator D accounts for 0.5 to 5 percent of the weight of the component B;
the balance of tributyl phosphate,
wherein the bifunctional hybrid polythioether rubber is represented by formula (I):
R 1 can be represented by formula (II):
-[(-CH 2 -) a -O-] b -(CH 2 ) c - Ⅱ
a is 2 to 6; b is 1 to 6; c is 2 to 8;
R 2 is H or F;
m＝1～3；
n is 3 to 10.
2. The hybrid polythioether sealant according to claim 1, characterized in that: the bifunctional hybrid polythioether rubber is obtained by polymerizing a dimercapto-terminated compound and a diolefin-terminated phenylene compound in the presence of free radicals, wherein the dimercapto-terminated compound has a general formula: HS-R 1 -SH。
3. The hybrid polythioether sealant according to claim 2, wherein:
the structure of the diolefin end-capped phenylene compound is shown as the formula (III):
4. the hybrid polythioether sealant according to claim 3, characterized in that: the tetrafunctional hybrid polythioether rubber is obtained by polymerizing micromolecular polythioether rubber and tetraolefin-terminated fluorosilicone polymer in the presence of free radicals, wherein the micromolecular polythioether rubber has a general formula: HS-R 1 S-[-CH 2 CH 2 O(CH 2 CH 2 O) y CH 2 CH 2 SR 1 -S-] z -H。
5. The hybrid polythioether sealant according to claim 4, wherein: the tetraolefin-terminated fluorosilicone polymer has the general formula (VI):
6. the hybrid polythioether sealant according to claim 1, characterized in that: the filler is one of gas-phase silica and precipitated silica or a mixture of a plurality of substances.
7. The hybrid polythioether sealant according to claim 1, characterized in that: the plasticizer is one or a mixture of phthalic acid substances, chlorinated paraffin or tributyl phosphate.
8. The hybrid polythioether sealant according to claim 1, characterized in that: the coupling agent is one or a mixture of more of perfluoropropyltrimethoxysilane, perfluorooctyltriethoxysilane and heptadecafluorodecyltrimethoxysilane.
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