Highly functional composite polymer monomers, methods for their preparation, and applications

Abstract

The present invention discloses a highly functional composite polymer monomer, a method for manufacturing the same, and applications, and relates to the field of polymer polyol technology. The technical solution is as follows: a polyether polyol intermediate is obtained by reacting an initiator S1 with an epoxy compound under the action of a catalyst; a polyether / polyester ether polyol is produced by reacting the polyether polyol intermediate S2 with a hyperbranched polyester polyol as a composite initiator and reacting the epoxy compound under the action of a catalyst; and a highly functional composite polymer monomer is produced by reacting the polyether / polyester ether polyol S3 with an unsaturated isocyanate under the action of a catalyst. The present invention improves the functionality of polymer monomers through an initiator, improves the dispersibility of polymer monomers in polymer polyols, improves the stability of styrene-acrylonitrile copolymer particles in polymer polyols, lowers the viscosity of polymer polyols, increases the proportion of hydrophobic groups in polymer polyols by introducing a polyester system into the polymer monomer structure, and reduces the occurrence of gelation when in contact with water.

Description

Technology Field

[0001] The present invention relates to the field of polymer polyol technology, and specifically to a highly functional composite polymer monomer and a method for manufacturing the same and its applications. Background Technology

[0002] Flexible polyurethane foam materials are widely applied in everyday life fields such as carpets, furniture, and transportation. Polymer particles within polymer polyols (POPs) are filled into the polyurethane network structure to effectively improve the pore size, hardness, and load-bearing capacity of flexible polyurethane foams; however, the viscosity of POPs increases significantly with an increase in polymer particle content (i.e., an increase in solid content). Currently, commercially available POP products have a solid content of less than 50% and a viscosity of less than 6,000 mPa·s. Polymer monomers are the core components of polymer polyols, and their amphiphilic structure exhibits excellent compatibility with base polyether polyols on the one hand, while on the other, it can improve the dispersibility of styrene-acrylonitrile copolymers in polyether media. Therefore, the structure of polymer monomers significantly influences the performance of polymer polyols, such as viscosity, storage stability, and gelling properties. Chinese invention patent CN111732707B discloses a type of polymer monomer stabilizer and its manufacturing method and application. By introducing a nitrogen-containing ring, the stability of the polymer polyol is effectively enhanced through dispersion force interactions with olefinic unsaturated monomers, and the manufactured polymer polyol has the advantages of low viscosity and uniform particle distribution.

[0003] It is generally known that highly functional polymer monomers exhibit excellent dispersion effects in POP, and a common method to reduce the viscosity of POP is to synthesize polymer monomers using highly functional polyether polyols. For example, Chinese invention patent CN112708124A discloses a method for manufacturing a type of highly functional polyether polyol and its application, which improved the functionality of the polyether polyol by adopting the copolymerization of epoxyalkanol and propylene oxide; however, since epoxyalkanols are toxic, they are subject to certain limitations in actual production. Furthermore, water is added as a chemical blowing agent in the polymer foaming process, but typically, adding water significantly increases the viscosity of the material. Chinese invention patent CN109796575B discloses a stabilizer and a method for manufacturing the same, a method for manufacturing a polymer polyol, and an application thereof. By utilizing multiple urethane bonds in the stabilizer, the gelling properties of POP are reduced, and the manufactured polymer polyol maintains excellent fluidity even in polyurethane foaming systems with high moisture content (moisture content of 3% or more). Therefore, reducing the viscosity and gelling properties of POP and improving hydrophobicity through the structural design of polymer monomers has become an urgent task for the industry. The problem to be solved

[0004] The technical problem that the present invention aims to solve is to overcome the shortcomings of conventional technology and to provide a highly functional composite polymer monomer and a method for manufacturing the same and its application. This involves improving the functionality of the polymer monomer through the high functionality of the initiator, and further enhancing the dispersion of the polymer monomer in the polymer polyol to improve the stability of styrene-acrylonitrile copolymer particles in the polymer polyol and lower the viscosity of the polymer polyol; and increasing the proportion of hydrophobic groups in the polymer polyol and reducing the occurrence of gelation by introducing a polyester system into the polymer monomer structure. means of solving the problem

[0005] The technical solution of the present invention is as follows.

[0006] In a first aspect, the present invention provides a method for producing a highly functional composite polymer monomer, and

[0007] A step of obtaining a polyether polyol intermediate by reacting an S1 initiator with an epoxy compound under the action of a catalyst;

[0008] S2. A step of producing a polyether / polyester ether polyol by reacting the polyether polyol intermediate obtained in S1 and the hyperbranched polyester polyol with an epoxy compound under the action of a catalyst using a composite initiator; and

[0009] S3 includes a step of reacting the polyether / polyester ether polyol obtained in S2 with an unsaturated isocyanate under the action of a catalyst to produce a highly functional composite polymer monomer.

[0010] Preferably, in step S1, the initiator is one or two of sucrose, solid sorbitol, and liquid sorbitol, the catalyst is KOH, the number average molecular weight of the polyether polyol intermediate is 900 to 2000 g / mol, the mass ratio of the initiator to the epoxy compound is 1:(4 to 8.5), and the catalyst accounts for 0.2 to 0.55% of the total mass of the initiator, catalyst, and epoxy compound.

[0011] Preferably, in step S2, the hyperbranched polyester polyol is Boltorn H311 with a functionality of 23, the catalyst is a DMC catalyst, the molar ratio of the polyether polyol intermediate to the hyperbranched polyester polyol is (0.6 to 4.5):1, the hydroxyl value of the polyether / polyester ether polyol is 28 to 58 mgKOH / g and the functionality is 7 to 9, the mass ratio of the complex initiator to the epoxy compound is 1:(3.6 to 7.3), and the catalyst accounts for 30 to 170 ppm of the total mass of the complex initiator, catalyst, and epoxy compound.

[0012] Preferably, in step S3, the unsaturated isocyanate is 3-isopropyl-dimethylbenzyl isocyanate, 2-methacryloyloxyethyl isocyanate or isocyanatoethyl acrylate, the catalyst is bismuth neodecanoate, the reaction temperature is 70 to 90°C, the molar ratio of polyether / polyester ether polyol to unsaturated isocyanate is (0.9 to 1.2):1, and the catalyst accounts for 50 to 100 ppm of the total mass of polyether / polyester ether polyol, unsaturated isocyanate, and catalyst.

[0013] Preferably, in step S1, the epoxy compound is propylene oxide and the reaction temperature is 100 to 140°C, and in step S2, the epoxy compound is propylene oxide and ethylene oxide and the reaction temperature is 100 to 140°C.

[0014] In a second aspect, the present invention provides a highly functional composite polymer monomer, which is produced by the method for producing the highly functional composite polymer monomer described above.

[0015] In a third aspect, the present invention provides an application of a highly functional composite polymer monomer, using the highly functional composite polymer monomer in the production of a polymer polyol, specifically,

[0016] (1) A step of obtaining a preliminary reaction product by synthesizing the aforementioned highly functional composite polymer monomer and olefinic unsaturated monomer under the action of a chain transfer agent and an initiator; and

[0017] (2) A step of obtaining a polymer polyol by adding an initiator, a base polyether polyol, and an olefinic unsaturated monomer to the pre-reactor obtained in step (1) and reacting them.

[0018] Preferably, the chain transfer agent in step (1) is isopropanol.

[0019] Preferably, in steps (1) and (2), the initiator is dimethyl 2,2'-azobisisobutyrate, and in step (1), the olefinic unsaturated monomers are styrene and acrylonitrile, with styrene accounting for 50% of the mass of the olefinic unsaturated monomers, and in step (2), the olefinic unsaturated monomers are styrene and acrylonitrile, with styrene accounting for 80% of the mass of the olefinic unsaturated monomers.

[0020] Preferably, in step (1), the chain transfer agent accounts for 60% of the total mass of the chain transfer agent, initiator, high-functionality composite polymer monomer, and olefinic unsaturated monomer, the initiator accounts for 0.1% of the total mass of the chain transfer agent, initiator, high-functionality composite polymer monomer, and olefinic unsaturated monomer, the high-functionality composite polymer monomer accounts for 24% of the total mass of the chain transfer agent, initiator, high-functionality composite polymer monomer, and olefinic unsaturated monomer, and the olefinic unsaturated monomer accounts for 15.9% of the total mass of the chain transfer agent, initiator, high-functionality composite polymer monomer, and olefinic unsaturated monomer, and in step (2), the initiator accounts for 0.25% of the total mass of the pre-reactor, initiator, base polyether polyol, and olefinic unsaturated monomer, and the pre-reactor consists of the pre-reactor, initiator, base polyether polyol, and The olefinic unsaturated monomer accounts for 12.5% ​​of the total mass, the base polyether polyol accounts for 40% of the total mass of the pre-reactor, initiator, base polyether polyol, and olefinic unsaturated monomer, and the olefinic unsaturated monomer accounts for 47.25% of the total mass of the pre-reactor, initiator, base polyether polyol, and olefinic unsaturated monomer. Effects of the invention

[0021] The present invention has the following beneficial effects compared to the prior art.

[0022] The present invention improves the functionality of polymer monomers through hyperbranched polyester polyols and stabilizes polymer polyol particles, reduces viscosity, and enhances filtration performance by forming a dendritic structure within the polymer polyol to provide a larger volume. Simultaneously, ester functional groups are introduced via an initiator, and urethane bonds are introduced via unsaturated isocyanates in terminal block polymerization. By improving the hydrophobicity of the polymer polyol through the two aforementioned types of ester bonds, the effect of viscosity increase after water addition during subsequent polymer polyol foaming is reduced. Specific details for implementing the invention

[0023] In order to enable a person skilled in the art to better understand the technical solution of the present invention, the technical solution of the present invention is described clearly and completely below in combination with embodiments of the present invention.

[0024] The raw materials used in the embodiments of the present invention are as follows:

[0025] Base polyether polyol: Soft foamed polyether polyol prepared by the reaction of glycerol, propylene oxide, and ethylene oxide, F5631, Shandong Yinuowei New Material Co., Ltd.;

[0026] Liquid Sorbitol, VC Grade, Shandong Tianli (Shandong Tianli Pharmaceutical Co., Ltd.);

[0027] Solid sorbitol, Shouguang Zhongrui Biotechnology Co., Ltd.;

[0028] Sucrose, weight group (COFCO);

[0029] Superbranched polyester polyol, Boltorn H311.

[0030] In the present invention, the method for measuring the performance of a polymer polyol is as follows:

[0031] Viscosity: Measured using a rotational viscometer equipped with a constant temperature bath, and the measurement temperature is 25℃.

[0032] Solid content: The base polyether polyol in the polymer polyol is washed with anhydrous ethanol, centrifuged, and repeated at least three times, and weighed in a constant temperature dryer until a constant weight is reached.

[0033] Screen passage time: Heat the polymer polyol to 100°C, feed 200g of polymer polyol into a 200 mesh screen, and record the time it takes for the polymer polyol to completely pass through the screen by gravity.

[0034] Example 1 Preparation of Polyether Polyol Intermediate 1

[0035] 180 g of solid sorbitol, 2 g of sucrose, and 5 g of KOH were introduced into a pressure reactor, heated to 100°C and dehydrated for 3 hours, then 740 g of propylene oxide was slowly added, the reaction temperature was controlled to 100°C, pressure was maintained for 1 hour after addition was complete, the monomer was removed under vacuum for 0.5 hours, then cooled to 90°C, 11.5 g of phosphoric acid and 32.5 g of water were added to neutralize, then 2 g of magnesium aluminum silicate was added as an adsorbent, and dehydrated and dried. The hydroxyl value of the obtained polyether polyol intermediate 1 was measured to be 374.5 mgKOH / g.

[0036] Example 2 Preparation of Polyether Polyol Intermediate 2

[0037] 91g of solid sorbitol, 130g of liquid sorbitol, and 5g of KOH were introduced into a pressure reactor, heated to 100°C and dehydrated for 6 hours, then 1850g of propylene oxide was slowly added, the reaction temperature was controlled to 120°C, pressure was maintained for 1 hour after addition was complete, the monomer was removed under vacuum for 0.5 hours, then cooled to 90°C, 22.8g of phosphoric acid and 32.5g of water were added to neutralize, then 2g of magnesium aluminum silicate was added as an adsorbent, and dehydrated and dried. The hydroxyl value of the obtained polyether polyol intermediate 2 was measured to be 168.2mgKOH / g.

[0038] Example 3 Preparation of Polyether Polyol Intermediate 3

[0039] 182 g of solid sorbitol and 6.2 g of KOH were introduced into a pressure reactor, heated to 100°C and dehydrated for 3 hours, then 1360 g of propylene oxide was slowly added, the reaction temperature was controlled to 140°C, pressure was maintained for 2 hours after addition was complete, the monomer was removed by vacuum for 1 hour, then cooled to 90°C, 18.8 g of phosphoric acid and 52 g of water were added to neutralize, then 2 g of magnesium aluminum silicate was added as an adsorbent, and dehydrated and dried. The hydroxyl value of the obtained polyether polyol intermediate 2 was measured to be 225.6 mgKOH / g.

[0040] Example 4 Preparation of Polyether / Polyester Ether Polyol 1

[0041] 80 g of polyether polyol intermediate 1 and 65 g of Boltorn H311 were introduced into a pressure reactor, heated to 100°C and maintained for 3 hours, then 0.2 g of DMC catalyst was added and dehydrated for another 1 hour, then 36 g of propylene oxide was added dropwise to initiate the polymerization reaction, and a mixed liquid of 840 g of propylene oxide and 180 g of ethylene oxide was additionally introduced. After the introduction was completed, the pressure was maintained for 1 hour, and the monomer was removed for 0.5 hours before being discharged. The hydroxyl value of the obtained polyether / polyester ether polyol 1 was 37.4 mgKOH / g, the functionality was 8, and the viscosity was 3750 mPa·s.

[0042] Example 5 Preparation of Polyether / Polyester Ether Polyol 2

[0043] 74 g of polyether polyol intermediate 1 and 120 g of Boltorn H311 were introduced into a pressure reactor, heated to 130°C and maintained for 3 hours, then 0.03 g of DMC catalyst was added and dehydrated for another hour, then 32 g of propylene oxide was added dropwise to initiate the polymerization reaction, and a mixed liquid of 540 g of propylene oxide and 135 g of ethylene oxide was additionally introduced. After the introduction was completed, the pressure was maintained for 1 hour, and the monomer was removed for 0.5 hours before being discharged. The hydroxyl value of the obtained polyether / polyester ether polyol 2 was 57.5 mgKOH / g, the functionality was 9, and the viscosity was 2010 mPa·s.

[0044] Example 6 Preparation of Polyether / Polyester Ether Polyol 3

[0045] 141 g of polyether polyol intermediate 3 and 32.4 g of Boltorn H311 were introduced into a pressure reactor, heated to 140°C and maintained for 3 hours, then 0.1 g of DMC catalyst was added and dehydrated for another hour, then 30 g of propylene oxide was added dropwise to initiate the polymerization reaction, and a mixed liquid of 990 g of propylene oxide and 210 g of ethylene oxide was additionally introduced. After the introduction was completed, the pressure was maintained for 1 hour, and after removing monomers for 0.5 hours, the product was discharged. The hydroxyl value of the obtained polyether / polyester ether polyol 3 was 28 mgKOH / g, the functionality was 7, and the viscosity was 2345 mPa·s.

[0046] Example 7 Preparation of Highly Functional Composite Polymer Monomer A

[0047] 1080 g of polyether / polyester ether polyol 1 and 20.1 g of 3-isopropyl-dimethylbenzyl isocyanate were introduced into a pressure reactor, 0.056 g of bismuth neodecanoate was added, the temperature was raised to 80°C, and 2261 cm⁻¹ by infrared spectroscopy - Highly functional composite polymer monomer A is prepared by setting the reaction endpoint when the peak at ¹ disappears.

[0048] Example 8 Preparation of Highly Functional Composite Polymer Monomer B

[0049] 1320 g of polyether / polyester ether polyol 1 and 20.1 g of 3-isopropyl-dimethylbenzyl isocyanate were introduced into a pressure reactor, 0.13 g of bismuth neodecanoate was added, the temperature was raised to 70°C, and 2261 cm⁻¹ by infrared spectroscopy - Highly functional composite polymer monomer B is prepared by setting the reaction endpoint when the peak at ¹ disappears.

[0050] Example 9 Preparation of Highly Functional Composite Polymer Monomer C

[0051] 900 g of polyether / polyester ether polyol 2 and 15.5 g of 2-methacryloyloxyethyl isocyanate were introduced into a pressure reactor, 0.09 g of bismuth neodecanoate was added, the temperature was raised to 80°C, and 2261 cm⁻¹ by infrared spectroscopy - Highly functional composite polymer monomer C is prepared by setting the reaction endpoint when the peak at ¹ disappears.

[0052] Example 10 Preparation of Highly Functional Composite Polymer Monomer D

[0053] 1400 g of polyether / polyester ether polyol 3 and 14.1 g of isocyanatoethyl acrylate were introduced into a pressure reactor, 0.11 g of bismuth neodecanoate was added, the temperature was raised to 90°C, and 2261 cm⁻¹ by infrared spectroscopy - Highly functional composite polymer monomer D is prepared by setting the reaction endpoint when the peak at ¹ disappears.

[0054] Comparative Example 1 Preparation of polymer monomer E

[0055] 1080 g of polyether polyol intermediate 1 was introduced into a pressure reactor, 0.04 g of DMC catalyst was added, and dehydration was carried out for 1 hour. Then, 37 g of propylene oxide was added dropwise to initiate the polymerization reaction, and a mixed liquid of 910 g of propylene oxide and 183 g of ethylene oxide was additionally introduced. After the introduction was completed, the pressure was maintained for 1 hour, and the monomer was removed for 0.5 hours before being discharged. The hydroxyl value of the obtained polyether polyol was 28.3 mgKOH / g, and the viscosity was 3853 mPa·s.

[0056] 1074g of the above polyether polyol and 20.1g of 3-isopropyl-dimethylbenzyl isocyanate were introduced into a pressure reactor, and after adding 0.06g of bismuth neodecanoate, the temperature was raised to 80℃, and 2261cm² by infrared spectroscopy - Polymer monomer E is prepared by setting the reaction endpoint when the peak at ¹ disappears.

[0057] Comparative Example 2 Preparation of Polymer Monomer F

[0058] 200g of polyether polyol intermediate 2 was introduced into a pressure reactor, 0.04g of DMC catalyst was added, and dehydration was carried out for 1 hour. Then, 32g of propylene oxide was added dropwise to initiate the polymerization reaction, and a mixed liquid of 1150g of propylene oxide and 180g of ethylene oxide was additionally introduced. After the introduction was completed, the pressure was maintained for 1 hour, and the monomer was removed for 0.5 hours before being discharged. The hydroxyl value of the obtained polyether polyol was 28.6mgKOH / g, and the viscosity was 2903mPa·s.

[0059] 1180g of the above polyether polyol and 15.5g of 2-methacryloyloxyethyl isocyanate were introduced into a pressure reactor, 0.05g of zinc neodecanoate was added, the temperature was raised to 80℃, and 2261cm² by infrared spectroscopy - Polymer monomer F is prepared by setting the reaction endpoint when the peak at ¹ disappears.

[0060] Comparative Example 3 Preparation of Polymer Monomer G

[0061] 2000g of the polyether polyol of Comparative Example 2 and 16.5g of maleic anhydride were introduced into a reactor, the temperature was raised to 150℃ to perform an esterification reaction, and after maintaining the temperature for 3 hours, 3g of KOH was added and the reaction was continued for another 3 hours, 30g of ethylene oxide was added and the reaction was continued, and after confirming that the acid value <0.5mgKOH / g, the mixture was released to produce polymer monomer G.

[0062] Preparation of polymer polyols:

[0063] (1) Preparation of preliminary reactants

[0064] The prepared polymer monomers A, B, C, D, E, F, and G were each introduced into a mixing tank along with a mixture of isopropanol, styrene (SM), and acrylonitrile (AN), and the initiator dimethyl 2,2'-azobisisobutyrate. The materials in the mixing tank were then transferred to a static mixer via a metering pump and sequentially fed into two series-connected pressure reactors to perform polymerization. The set reaction temperature of the two pressure reactors was 110°C, and the residence time of the materials in each reactor was 60 minutes. Finally, preliminary reactants PA, PB, PC, PD, PE, PF, and PG were obtained, respectively. The preliminary reactants PA, PB, PC, PD, PE, PF, and PG were cooled using a cooler, collected, and stored. The mass percentages of the polymer monomers, the mixture of isopropanol, styrene, and acrylonitrile, and the initiator are shown in Table 1:

[0065] Table 1 Mass percentages of polymer monomer, isopropanol, styrene and acrylonitrile mixture and initiator

[0066]

[0067] (2) Preparation of polymer polyols

[0068] Pre-reactants PA, PB, PC, PD, PE, PF, and PG are each introduced into a mixing tank along with a base polyether polyol, a mixture of styrene and acrylonitrile, and the initiator dimethyl 2,2'-azobisisobutyrate. The materials in the mixing tank are then transferred to a static mixer via a metering pump and subsequently fed sequentially into the first and second internal pressure reactors through an input pipe for reaction. The set reaction temperature of both internal pressure reactors is 125°C, and the residence time of the materials in each reactor is 60 minutes. The crude product exiting the second internal pressure reactor is fed into a demonomerization reactor to remove unreacted volatile matter under vacuum, thereby finally obtaining polymer polyol 1-7. The mass percentages of the pre-reactants, base polyether polyol, mixture of styrene and acrylonitrile, and initiator are as shown in Table 2:

[0069] Table 2 Mass percentages of pre-reactants, base polyether polyols, mixtures of styrene and acrylonitrile, and initiators

[0070]

[0071] Performance tests were performed on polymer polyols 1-7, and the test results are as shown in Table 3:

[0072] Table 3 Performance test results of polymer polyols 1-7

[0073]

[0074] As can be seen in Table 3, compared to polymer polyols 5-7 prepared with polymer monomer EG of Comparative Examples 1-3, polymer polyol 1-4 prepared with polymer monomer AD of Examples 7-10 showed significantly lower viscosity, significantly shortened filtration time, and reduced viscosity increase after water addition. This is because the high-functionality composite polymer monomer prepared in Examples 7-10 had a larger dispersion volume within the polymer polyol, thereby improving the stability of the polymer polyol.

Claims

Claim 1 A method for producing a highly functional composite polymer monomer, comprising: S1: a step of reacting an initiator with an epoxy compound under the action of a catalyst to obtain a polyether polyol intermediate; S2: a step of reacting the polyether polyol intermediate obtained in step S1 with a hyperbranched polyester polyol with an epoxy compound under the action of a catalyst using a composite initiator to produce a polyether and a polyester ether polyol; and S3: a step of reacting the polyether and polyester ether polyol obtained in step S2 with an unsaturated isocyanate under the action of a catalyst to produce a highly functional composite polymer monomer. Claim 2 A method for preparing a highly functional composite polymer monomer, characterized in that, in step S1, the initiator is one or two of sucrose, solid sorbitol, and liquid sorbitol, the catalyst is KOH, the number average molecular weight of the polyether polyol intermediate is 900 to 2000 g / mol, the mass ratio of the initiator to the epoxy compound is 1:(4 to 8.5), and the catalyst accounts for 0.2 to 0.55% of the total mass of the initiator, catalyst, and epoxy compound. Claim 3 A method for producing a highly functional composite polymer monomer, wherein, in claim 1, the catalyst in step S2 is a DMC catalyst; the molar ratio of the polyether polyol intermediate to the hyperbranched polyester polyol is (0.6 to 4.5):1, the hydroxyl value of the polyether and polyester ether polyol is 28 to 58 mgKOH / g and the functionality is 7 to 9, the mass ratio of the composite initiator to the epoxy compound is 1:(3.6 to 7.3), and the catalyst accounts for 30 to 170 ppm of the total mass of the composite initiator, catalyst, and epoxy compound. Claim 4 A method for preparing a highly functional composite polymer monomer, characterized in that, in step S3, the unsaturated isocyanate is 3-isopropyl-dimethylbenzyl isocyanate, 2-methacryloyloxyethyl isocyanate, or isocyanatoethyl acrylate, the catalyst is bismuth neodecanoate, the reaction temperature is 70 to 90°C, the molar ratio of polyether and polyester ether polyol to unsaturated isocyanate is (0.9 to 1.2):1, and the catalyst accounts for 50 to 100 ppm of the total mass of polyether and polyester ether polyol, unsaturated isocyanate, and catalyst. Claim 5 A method for preparing a highly functional composite polymer monomer, characterized in that, in step S1, the epoxy compound is propylene oxide and the reaction temperature is 100 to 140°C, and in step S2, the epoxy compound is propylene oxide and ethylene oxide and the reaction temperature is 100 to 140°C. Claim 6 A highly functional composite polymer monomer characterized by being manufactured by a method for manufacturing a highly functional composite polymer monomer according to any one of claims 1 to 5. Claim 7 A method for producing a polymer polyol using a highly functional composite polymer monomer according to claim 6, comprising: (1) a step of obtaining a preliminary reaction product by synthesizing the highly functional composite polymer monomer according to claim 6 and an olefinic unsaturated monomer under the action of a chain transfer agent and an initiator; and (2) a step of obtaining a polymer polyol by adding an initiator, a base polyether polyol, and an olefinic unsaturated monomer to the preliminary reaction product obtained in step (1) and reacting them. Claim 8 A method according to claim 7, characterized in that the chain transfer agent in step (1) is isopropanol. Claim 9 A method according to claim 7, wherein in steps (1) and (2), the initiator is dimethyl 2,2'-azobisisobutyrate, in step (1), the olefinic unsaturated monomers are styrene and acrylonitrile and styrene accounts for 50% of the mass of the olefinic unsaturated monomers, and in step (2), the olefinic unsaturated monomers are styrene and acrylonitrile and styrene accounts for 80% of the mass of the olefinic unsaturated monomers. Claim 10 In claim 7, in step (1), the chain transfer agent accounts for 60% of the total mass of the chain transfer agent, initiator, high-functionality composite polymer monomer, and olefinic unsaturated monomer, the initiator accounts for 0.1% of the total mass of the chain transfer agent, initiator, high-functionality composite polymer monomer, and olefinic unsaturated monomer, the high-functionality composite polymer monomer accounts for 24% of the total mass of the chain transfer agent, initiator, high-functionality composite polymer monomer, and olefinic unsaturated monomer, and the olefinic unsaturated monomer accounts for 15.9% of the total mass of the chain transfer agent, initiator, high-functionality composite polymer monomer, and olefinic unsaturated monomer, and in step (2), the initiator accounts for 0.25% of the total mass of the pre-reactor, initiator, base polyether polyol, and olefinic unsaturated monomer, and the pre-reactor is a pre-reactor, initiator, base polyether polyol, and A method characterized by the olefinic unsaturated monomer accounting for 12.5% ​​of the total mass, the base polyether polyol accounting for 40% of the total mass of the pre-reactor, initiator, base polyether polyol, and olefinic unsaturated monomer, and the olefinic unsaturated monomer accounting for 47.25% of the total mass of the pre-reactor, initiator, base polyether polyol, and olefinic unsaturated monomer.

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