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CN111718480A - Acryloyloxy polyether curing agent - Google Patents

Acryloyloxy polyether curing agent Download PDF

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CN111718480A
CN111718480A CN202010619112.0A CN202010619112A CN111718480A CN 111718480 A CN111718480 A CN 111718480A CN 202010619112 A CN202010619112 A CN 202010619112A CN 111718480 A CN111718480 A CN 111718480A
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curing agent
methyl glycoluril
polyether
tetrahydroxy
polypropylene oxide
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CN111718480B (en
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莫洪昌
卢先明
徐明辉
张倩
段秉蕙
王伯周
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Xian Modern Chemistry Research Institute
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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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
    • C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
    • C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
    • C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • 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
    • C09J11/08—Macromolecular additives
    • 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
    • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
    • C09J171/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another

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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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  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Polyethers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention discloses a terminal acryloxy polyether curing agent, which has the following structural formula:

Description

Acryloyloxy polyether curing agent
Technical Field
The invention relates to a curing agent of a solid propellant, in particular to an end acryloxy polyether curing agent, belonging to the field of solid propellants.
Background
Polyazidoglycidyl ether (GAP) has the advantages of positive heat of formation, fast combustion, high energy, clean fuel gas, good thermal stability, low mechanical sensitivity and the like, and is an ideal adhesive for high-energy low-characteristic signal propellants, fuel gas generators and high-solid-content propellant. GAP is generally used together with an isocyanate curing agent, and polyurethane elastomer is prepared by reaction and curing of terminal hydroxyl and isocyanate groups, but the isocyanate curing agent in the curing system has high activity, is easy to react with water or protonic acid rapidly to generate CO2, forms many pores in the curing process of the propellant, reduces the density of the propellant, influences the mechanical property of the propellant, and simultaneously reduces the safety and the reliability of the propellant.
In order to solve the problems of the isocyanate curing agent, researchers develop an alkynyl curing agent, namely, the alkynyl in the alkynyl curing agent and azido on a GAP side chain are subjected to curing and crosslinking reaction to prepare the polytriazole crosslinking elastomer. For example, Thomas Keicher et al Isocynate-free curing of glycidyl-azide-polymer (GAP) with bis-propyl-succinate
39th Int Annu Conf of ICT,2008 discloses an alkynyl curing agent, dipropynyl succinate (BPS), having the following structural formula:
Figure BDA0002562403310000011
the GAP can adopt BPS to cure to prepare the polytriazole crosslinked elastomer, and the dosage of the BPS has larger influence on the mechanical property of the elastomer. When the amount of BPS is 8.97%, the mechanical property of the elastomer obtained by curing is optimal: the tensile strength is 0.215MPa, the elongation is 44.68%, and the mechanical properties of the elastomer such as the tensile strength, the elongation and the like are still low.
Disclosure of Invention
In order to solve the defects or technical defects in the prior art, the invention provides the terminal acryloxy polyether curing agent capable of endowing the GAP-based crosslinked elastomer with higher mechanical property.
In order to solve the technical problems, the structural formula of the terminal acryloyloxy polyether curing agent is as follows:
Figure BDA0002562403310000021
wherein x + y + m + n is 12-40 and is an integer.
The synthesis route of the terminal acryloyloxy polyether curing agent is as follows:
Figure BDA0002562403310000022
wherein x + y + m + n is 12-40 and is an integer.
The synthesis method of the terminal acryloyloxy polyether curing agent comprises the following steps:
(1) initiating the ring-opening polymerization of propylene oxide by using 1,3,4, 6-tetrahydroxy methyl glycoluril as an initiator, boron trifluoride-diethyl ether complex as a catalyst and dichloromethane as a solvent to obtain 1,3,4, 6-tetrahydroxy polypropylene oxide methyl glycoluril; the mol ratio of the epoxypropane, the boron trifluoride-diethyl ether complex and the 1,3,4, 6-tetramethylolglycoluril is 12-40: 0.5-2: 1, and the reaction temperature is 15-30 ℃.
(2)1,3,4, 6-tetrahydroxy polypropylene oxide methyl glycoluril and acryloyl chloride are used as raw materials, triethylamine is used as a catalyst, dichloromethane is used as a solvent, and acylation reaction is carried out to obtain 1,3,4, 6-tetraacryloxy polypropylene oxide methyl glycoluril (T-PAPO for short), namely the terminal acryloyloxy polyether curing agent; the molar ratio of triethylamine, acryloyl chloride and 1,3,4, 6-tetrahydroxy polypropylene oxide methyl glycoluril is 4.4-6.0: 4.4-5.2: 1, and the reaction temperature is-5 ℃ to 5 ℃.
The invention has the beneficial effects that:
the T-PAPO curing agent can be used for curing azide adhesives such as GAP and the like, can also be used for curing azido polyether (or polyester) adhesives such as azido ethylene oxide-tetrahydrofuran copolyether and the like, and contains a strong polar glycoluril ring unit, a flexible polypropylene oxide chain or a plurality of active acryloyl oxygen groups in the molecule of the T-PAPO curing agent. On one hand, the acting force between hard chain segments can be enhanced, the microphase separation of the elastomer is promoted, on the other hand, the chain segment length between crosslinking points and the crosslinking density of the elastomer can be increased, and the mechanical property of the elastomer is improved. The T-PAPO/GAP crosslinked elastomer has the tensile strength of 0.862MPa at 20 ℃ and the elongation of 82.11 percent; the BPS/GAP crosslinked elastomer in the reference has a tensile strength of 0.215MPa at 20 ℃ and an elongation of 44.68%.
Detailed Description
The technical mechanism of the invention is as follows: the reasons that the GAP-based polytriazole crosslinked elastomer has low mechanical properties are that BPS is a small-molecular curing agent, the interaction between polytriazole hard chain segments in the cured elastomer is weak, microphase separation is not facilitated, and chain segments between triazole crosslinking points are short. In order to improve the mechanical property of the elastomer, the invention comprises the following steps: (1) a glycoluril ring unit with strong polarity is introduced into the curing agent, so that the acting force between hard chain segments is enhanced, the microphase separation of the elastomer is promoted, and the tensile strength is improved; (2) a flexible polypropylene oxide chain segment is introduced into the curing agent, so that the chain segment length between triazole cross-linking points is increased, and the elongation is improved; (3) a plurality of acryloyl oxygen groups are introduced into the curing agent, so that the curing reaction activity and the crosslinking density of the elastomer are improved.
The present invention will be described in further detail with reference to examples.
Testing an instrument:
(1) the infrared spectrum is tested by a Nexus 870 Fourier transform infrared spectrometer of Nicolet company in the United states;
(2) the hydroxyl value was measured by phthalic anhydride-pyridine acylation.
(3) Number average molecular weight
Equipment: GPC-50 gel permeation chromatography of PL corporation, UK;
GPC test conditions: the chromatographic column is series connected by PLGel MIXED-E; the mobile phase is THF; the column temperature was 40 ℃; the detector is a differential refractive detector.
(4) Mechanical properties
Equipment: universal materials testing machine model Instron 4505, Instron corporation, usa;
the test method comprises the following steps: the stretching rate is 100mm/min, according to GJB770B-2005 method 413.1.
Example 1
(1) Synthesis of 1,3,4, 6-tetrahydroxy polypropylene oxide methyl glycoluril
In a four-necked round-bottomed flask equipped with a mechanical stirrer, a thermometer, a reflux condenser and a dropping funnel, 2.62g (0.01mol) of 1,3,4, 6-tetramethylolglycoluril and 20mL of CH were charged at 20 deg.C2Cl2Adding 0.85g (0.006mol) of boron trifluoride-diethyl ether complex under stirring, stirring for 30min, slowly dropwise adding 11.62g (0.2mol) of propylene oxide, reacting for 24 hr, and adding 2% Na2CO3The reaction was terminated with 20mL of aqueous solution, the organic phase was separated with a separatory funnel, washed with water to neutrality, and concentrated under reduced pressure to give a pale yellow viscous liquid.
And (3) structural identification:
IR，νmax(cm-1)：3443(-OH)，2966、2847(－CH3、－CH2) 1700, 1300 (glycoluril ring), 1112 (C-O-C).
Molecular weight and distribution: mn＝1420，Mw＝2102，Mw/Mn＝1.48。
Hydroxyl value: 156.44 mgKOH/g.
The above analytical data confirmed that the synthesized compound was 1,3,4, 6-tetrahydroxypropyleneoxide methyl glycoluril.
(2) Synthesis of 1,3,4, 6-tetraacryloxy polypropylene oxide methyl glycoluril
Adding 14.2g of 1,3,4, 6-tetrahydroxy polypropylene oxide methyl glycoluril, 150mL of dichloromethane and 5.06g of triethylamine into a reaction bottle at room temperature, stirring uniformly, cooling to 0 ℃, starting to slowly dropwise add 30mL of a dichloromethane solution of 4.52g of acryloyl chloride for 8h, continuing to react for 24h after dropwise addition, adding water to wash to neutrality, and concentrating an organic phase to obtain bright red viscous liquid.
And (3) structural identification:
IR，νmax(cm-1)：2966、2847(－CH3、－CH2) 1700, 1300 (glycoluril ring), 1732(C ═ O), 1635(C ═ C), 1112 (C-O-C).
Molecular weight and distribution: mn＝1632，Mw＝2432，Mw/Mn＝1.49。
Acryloyl group content: 2.42 mmol/g.
The above analytical data confirmed that the synthesized compound was 1,3,4, 6-tetraacryloxypolypropyleneoxide methylglycoluril.
The application performance of the terminal acryloyloxy polyether curing agent of the invention
(1) Miscibility and reactivity with adhesives
GAP and azido-terminated ethylene oxide-tetrahydrofuran copolyether (APET) are selected as the adhesive, and the miscibility and reactivity of the T-PAPO curing agent and the adhesive are examined.
The T-PAPO curing agent has good miscibility with two adhesives, namely GAP and APET, the mixture is clear and transparent, and the formed mixed solution can be stably subjected to curing reaction at the temperature of 60-70 ℃.
(2) Mechanical properties of elastomers
The T-PAPO curing agent of the present invention is reacted with GAP adhesive to produce poly triazoline crosslinked elastomer, and the corresponding mechanical properties are shown in Table 1.
TABLE 1 Effect of curing agent on mechanical Properties of elastomer (20 ℃ C.)
Figure BDA0002562403310000051
Therefore, the mechanical property of the poly-triazoline elastomer formed by the reaction of the T-PAPO curing agent and the GAP is obviously superior to that of the BPS-based poly-triazoline elastomer.

Claims (4)

1. An end acryloyl oxygen polyether curing agent, which is characterized in that: the structural formula is as follows:
Figure FDA0002562403300000011
wherein x + y + m + n is 12-40 and is an integer.
2. A process for preparing the acryloxy terminated polyether curative of claim 1, characterized by: the method comprises the following steps:
(1) initiating the ring-opening polymerization of propylene oxide by using 1,3,4, 6-tetrahydroxy methyl glycoluril as an initiator, boron trifluoride-diethyl ether complex as a catalyst and dichloromethane as a solvent to obtain 1,3,4, 6-tetrahydroxy polypropylene oxide methyl glycoluril;
(2) the method comprises the steps of carrying out acylation reaction on 1,3,4, 6-tetrahydroxy polypropylene oxide methyl glycoluril and acryloyl chloride serving as raw materials, triethylamine serving as a catalyst and dichloromethane serving as a solvent to obtain the 1,3,4, 6-tetraacryloxy polypropylene oxide methyl glycoluril, namely the terminal acryloyloxy polyether curing agent.
3. The method according to claim 2, wherein the molar ratio of the propylene oxide, the boron trifluoride-diethyl ether complex and the 1,3,4, 6-tetramethylolglycoluril in the step (1) is 12 to 40:0.5 to 2:1, and the reaction temperature is 15 to 30 ℃.
4. The preparation method according to claim 2, wherein the molar ratio of triethylamine, acryloyl chloride and 1,3,4, 6-tetrahydroxypolypropylene oxide methyl glycoluril in the step (2) is 4.4-6.0: 4.4-5.2: 1, and the reaction temperature is-5 ℃ to 5 ℃.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112920002A (en) * 2021-01-28 2021-06-08 西安近代化学研究所 Energy-containing terminal alkenyl polyether curing agent, preparation method and application
US11535707B1 (en) * 2018-08-14 2022-12-27 United States Of America As Represented By The Secretary Of The Army Process for preparing light curable energetic binder

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US4064191A (en) * 1976-03-10 1977-12-20 American Cyanamid Company Coating composition containing an alkylated glycoluril, a polymeric non-self-crosslinking compound and an acid catalyst
GB2010875A (en) * 1977-12-23 1979-07-04 American Cyanamid Co Polymeric Coating Compositions
US4299592A (en) * 1979-01-18 1981-11-10 Basf Aktiengesellschaft Printing of textile materials
JPS6487608A (en) * 1987-09-29 1989-03-31 Mitsui Petrochemical Ind Polymerizable compound containing aryloyloxyl group and methacryloyloxyl group in one molecule and curing agent
CN101460534A (en) * 2006-03-30 2009-06-17 加特微胶囊股份公司 Microcapsules comprising an acetyleneurea-polyurea polymer and controlled release formulations thereof
JP2010174241A (en) * 2008-12-29 2010-08-12 Sanyo Chem Ind Ltd Method for producing polyether
CN105085532A (en) * 2015-09-07 2015-11-25 山西医科大学 Tetrakisglycoluril derivative and preparation method thereof
JP2018053132A (en) * 2016-09-29 2018-04-05 四国化成工業株式会社 (Meth) acrylate compound, synthesis method thereof and use of the (meth) acrylate compound
CN109161012A (en) * 2018-09-13 2019-01-08 西安近代化学研究所 A kind of endlap nitrogen hexadecyl ethylene oxide-tetrahydrofuran block co-polyether and its synthetic method containing carbamate structures unit
CN110172142A (en) * 2019-06-26 2019-08-27 西安近代化学研究所 Acrylate-based client glycidol ether nitrate-tetrahydrofuran copolyether prepolymer
CN110183645A (en) * 2019-06-26 2019-08-30 西安近代化学研究所 A kind of light-cured type nitrate ester polyether and its synthetic method

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1379003A (en) * 1972-02-01 1975-01-02 Nobel Hoechst Chimie Compounds and methods for treatment of fabrics to give anti-stain properties
US4064191A (en) * 1976-03-10 1977-12-20 American Cyanamid Company Coating composition containing an alkylated glycoluril, a polymeric non-self-crosslinking compound and an acid catalyst
GB2010875A (en) * 1977-12-23 1979-07-04 American Cyanamid Co Polymeric Coating Compositions
US4299592A (en) * 1979-01-18 1981-11-10 Basf Aktiengesellschaft Printing of textile materials
JPS6487608A (en) * 1987-09-29 1989-03-31 Mitsui Petrochemical Ind Polymerizable compound containing aryloyloxyl group and methacryloyloxyl group in one molecule and curing agent
CN101460534A (en) * 2006-03-30 2009-06-17 加特微胶囊股份公司 Microcapsules comprising an acetyleneurea-polyurea polymer and controlled release formulations thereof
JP2010174241A (en) * 2008-12-29 2010-08-12 Sanyo Chem Ind Ltd Method for producing polyether
CN105085532A (en) * 2015-09-07 2015-11-25 山西医科大学 Tetrakisglycoluril derivative and preparation method thereof
JP2018053132A (en) * 2016-09-29 2018-04-05 四国化成工業株式会社 (Meth) acrylate compound, synthesis method thereof and use of the (meth) acrylate compound
CN109161012A (en) * 2018-09-13 2019-01-08 西安近代化学研究所 A kind of endlap nitrogen hexadecyl ethylene oxide-tetrahydrofuran block co-polyether and its synthetic method containing carbamate structures unit
CN110172142A (en) * 2019-06-26 2019-08-27 西安近代化学研究所 Acrylate-based client glycidol ether nitrate-tetrahydrofuran copolyether prepolymer
CN110183645A (en) * 2019-06-26 2019-08-30 西安近代化学研究所 A kind of light-cured type nitrate ester polyether and its synthetic method

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11535707B1 (en) * 2018-08-14 2022-12-27 United States Of America As Represented By The Secretary Of The Army Process for preparing light curable energetic binder
CN112920002A (en) * 2021-01-28 2021-06-08 西安近代化学研究所 Energy-containing terminal alkenyl polyether curing agent, preparation method and application

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