CN113121863A - Foaming composition and forming method of foaming material - Google Patents
Foaming composition and forming method of foaming material Download PDFInfo
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- CN113121863A CN113121863A CN201911403060.7A CN201911403060A CN113121863A CN 113121863 A CN113121863 A CN 113121863A CN 201911403060 A CN201911403060 A CN 201911403060A CN 113121863 A CN113121863 A CN 113121863A
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- 238000005187 foaming Methods 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 239000000463 material Substances 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 84
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 71
- -1 amino compound Chemical class 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 36
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 35
- 150000005676 cyclic carbonates Chemical class 0.000 claims abstract description 27
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 239000000945 filler Substances 0.000 claims description 50
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000004593 Epoxy Substances 0.000 claims description 16
- 239000004721 Polyphenylene oxide Chemical class 0.000 claims description 12
- 150000007824 aliphatic compounds Chemical group 0.000 claims description 12
- 150000001491 aromatic compounds Chemical group 0.000 claims description 12
- 229920000570 polyether Chemical class 0.000 claims description 9
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001334 alicyclic compounds Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 229920002873 Polyethylenimine Polymers 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052902 vermiculite Inorganic materials 0.000 claims description 3
- 235000019354 vermiculite Nutrition 0.000 claims description 3
- 239000010455 vermiculite Substances 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims 2
- 239000011325 microbead Substances 0.000 claims 2
- 229960001124 trientine Drugs 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 abstract description 6
- 150000002513 isocyanates Chemical class 0.000 abstract description 6
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- WPYCRFCQABTEKC-UHFFFAOYSA-N Diglycidyl resorcinol ether Chemical compound C1OC1COC(C=1)=CC=CC=1OCC1CO1 WPYCRFCQABTEKC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000498 cooling water Substances 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 239000004088 foaming agent Substances 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000006261 foam material Substances 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- YQMXOIAIYXXXEE-UHFFFAOYSA-N 1-benzylpyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC=CC=C1 YQMXOIAIYXXXEE-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- LVMMNTVTTXCQRQ-UHFFFAOYSA-N [3-(aminomethylidene)cyclohexylidene]methanamine Chemical compound NC=C1CC(CCC1)=CN LVMMNTVTTXCQRQ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
- C08J9/08—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing carbon dioxide
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/02—CO2-releasing, e.g. NaHCO3 and citric acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention provides a foaming composition comprising: 100 parts by weight of a cyclic carbonate-based compound and a blowing agent, wherein the blowing agent comprises: 3 to 13 parts by weight of a carbamate; and 15 to 65 parts by weight of an amino compound. The invention also provides a forming method of the foaming material, which comprises the following steps: mixing 100 parts by weight of a cyclic carbonate-based compound with a blowing agent to form a foaming composition, wherein the blowing agent comprises 3 to 13 parts by weight of a carbamate and 15 to 65 parts by weight of an amino compound; and heating the foaming composition to 100 ℃ to 170 ℃ to decompose the carbamate into carbon dioxide and an amino compound, and the amino compound reacts with the cyclic carbonate-based compound to form the foamed material. The foaming composition does not contain halogen and isocyanate, and meets the requirements of environmental protection and low toxicity.
Description
Technical Field
The present disclosure relates to foaming materials, and more particularly, to foaming compositions for forming foaming materials.
Background
The foamed material has quite wide application, wherein the polyurethane foamed material has excellent chemical resistance, solvent resistance, abrasion resistance and the like, so that the polyurethane foamed material has quite wide application in life or industry, particularly furniture, bedding, transportation, refrigerated buildings, heat insulation and the like. From the perspective of various polyurethane application fields and product distribution ratios all over the world, the light foamed products account for about six to half of all polyurethane markets, and the market demand is quite remarkable. The blowing agent used in the foaming process is an auxiliary agent added to form a cell structure in the plastic, i.e., to produce a foam structure. They can generate a large amount of gas under certain conditions to form a porous structure material with continuous or discontinuous pores (i.e., open or closed pores).
Currently, the conventional isocyanate foaming compositions are toxic, so that a new foaming composition is urgently needed to replace the application of isocyanate in foaming materials.
Disclosure of Invention
The object of the present invention is to provide a novel foaming composition which avoids the toxicity of the use of isocyanates.
An embodiment of the present disclosure provides a foaming composition, including: 100 parts by weight of a cyclic carbonate-based compound and a blowing agent. The foaming agent comprises: 3 to 13 parts by weight of a carbamate; and 15 to 65 parts by weight of an amino compound.
An embodiment of the present disclosure provides a method for forming a foam material, including: mixing 100 parts by weight of a cyclic carbonate-based compound with a blowing agent to form a foaming composition, wherein the blowing agent comprises 3 to 13 parts by weight of a carbamate, and 15 to 65 parts by weight of an amino compound; and heating the foaming composition to 100 ℃ to 170 ℃ to decompose the carbamate into carbon dioxide and an amino compound, and the amino compound reacts with the cyclic carbonate-based compound to form the foamed material.
Compared with the prior art, the invention has the advantages that: the foaming composition of the invention adopts carbamate to provide carbon dioxide (as a foaming agent) and carries out ring-opening reaction with cyclic carbonate, so the foaming composition does not contain halogen and isocyanate, and meets the requirements of environmental protection and low toxicity.
Detailed Description
An embodiment of the present disclosure provides a foaming composition, including: 100 parts by weight of a cyclic carbonate-based compound and a blowing agent, wherein the blowing agent comprises: 3 to 13 parts by weight of a carbamate salt, and 15 to 65 parts by weight of an amino compound. If the proportion of carbamate is too low, the foaming effect is insufficient. If the proportion of carbamate is too high, it tends to collapse and stick. If the proportion of the amino compound is too low, stickiness may occur. If the proportion of the amino compound is too high, stickiness may also occur. In some embodiments, the cyclic carbonate-based compound comprises an aliphatic cyclic carbonate-based compound, an alicyclic cyclic carbonate-based compound, an aromatic cyclic carbonate-based compound, or a combination thereof.
For example, the cyclic carbonate-based compound may have the structure
Wherein n is an integer from 1 to 6; r1Is aliphatic compound, alicyclic compound, aromatic compound, alkyl substituted aromatic compound, polyether oligomer, polyester oligomer or the combination of the above compounds; and R2Is H, an aliphatic compound containing a cyclic carbonate group, or a combination of the above.
In some embodiments, the cyclic carbonate-based compound may be 1,4-butanediol glycidyl ether cyclic carbonate (BDCE), diglycidyl resorcinol ether cyclic carbonate (RDCE), bisphenol a diol glycidyl ether cyclic carbonate (DABCE), polypropylene glycol diglycidyl ether cyclic carbonate (PPGDCE), cyclohexane-1, 2 dicarboxylic acid diglycidyl ester cyclic carbonate (DCCDC), 1, 4-cyclohexanedimethanol diglycidyl ether cyclic carbonate (CDCE), trimethylolpropane triglycidyl ether cyclic carbonate (PE300C), Mn 250 to 10000, epoxidized soybean oil cyclic Carbonate (CSBO), or a combination thereof.
In some embodiments, the carbamate is formed by reacting an amino compound with carbon dioxide and has the structure
R3Is C1～C12Polyether amines, alkyl amines, cycloalkyl amines, aryl amines, or combinations thereof. In one embodiment, the amino compound comprises a polyether amine, an alkyl amine, a cycloalkyl amine, an aryl amine, or a combination thereof. For example, the amino compound includes Triethylenetetramine (TETA), trimethylhexamethylenediamine (TETA)Trimethyomethyethylenediamine, TMD), polyethyleneimine (PEI 300), 1, 3-bis-methylamine cyclohexane (1,3-bis (aminomethylene) cyclohexane, 1,3-BAC), m-xylylenediamine (mXDA), polypropylenediamine, Polyoxypropylenediamine, Mn 200 to 4000, Polyetheramine, polyethylenamine, Mn 100 to 200, Ethylenediamine (EDA), or a combination thereof.
In some embodiments, the foaming composition further comprises 0.1 to 10 parts by weight of an epoxy compound, which may have a structure of
Wherein m is an integer from 1 to 6; r4Is aliphatic compound, alicyclic compound, aromatic compound, alkyl substituted aromatic compound, polyether oligomer, polyester oligomer or the combination of the above compounds; and R5Is H, an aliphatic compound containing a cyclic carbonate group, or a combination of the above. In some embodiments, the epoxy compound comprises an aliphatic epoxy compound, an alicyclic epoxy compound, an aromatic epoxy compound, or a combination thereof. The epoxy compound helps to improve the tensile strength and tear strength of the foamed material. If the proportion of the epoxy compound is too high, flexibility is lowered.
For example, epoxy compounds include 1,4-Butanediol Diglycidyl ether (1,4-Butanediol Diglycidyl ether, BDGE), Diglycidyl Resorcinol ether (RDGE), Bisphenol A diol glycidyl ether (Bisphenol A Diglycidyl ether, DABGE), Polypropylene glycol Diglycidyl ether (PPGDGE), cyclohexane-1, 2-dicarboxylic acid Diglycidyl ester (DGCDC), 1, 4-cyclohexanedimethanol Diglycidyl ether (1, 4-cyclohexanedicarboxylate), Trimethylolpropane triglycidyl ether (PE 300), epoxy soybean oil (Epsoybell oil, or combinations thereof.
In some embodiments, the foaming composition further comprises 2 to 10 parts by weight of a filler, and the filler comprises hollow microspheres, vermiculite or a combination thereof, and the material of the microspheres can be plastic, ceramic or glass. The filler may support the foam against collapse. If the amount of the filler is too high, the foaming density becomes too high.
An embodiment of the present disclosure provides a method for forming a foam material, including: 100 parts by weight of a cyclic carbonate-based compound and a foaming agent are mixed to form a foaming composition. The blowing agent comprises 3 to 13 parts by weight of carbamate, and 15 to 65 parts by weight of an amino compound. The composition and ratio of the foaming composition are as described above and will not be described in detail herein.
The foaming composition is then heated to 100 ℃ to 170 ℃ to decompose the carbamate into carbon dioxide and an amino compound, and the amino compound reacts with the cyclic carbonate-based compound to form the foamed material. If the temperature at which the foaming composition is heated is too low, the carbamate does not decompose into carbon dioxide and an amino compound, and therefore the foaming effect is not obtained. If the temperature of the foaming composition is heated too high, the foaming product will be severely broken.
As described above, the carbamate can provide carbon dioxide (as a blowing agent) and undergo a ring-opening reaction with the cyclic carbonate group. The foaming composition does not contain halogen and isocyanate, thereby meeting the requirements of environmental protection and low toxicity.
In order to make the aforementioned and other objects, features, and advantages of the present disclosure more comprehensible, preferred embodiments accompanied with figures are described in detail below:
[ examples ] A method for producing a compound
Synthesis example 1(CA-TETA)
TETA (150g) was taken and placed in a 2 liter jacketed glass reactor to mechanically stir the reaction solution and to which carbon dioxide (20 Kg/cm) was passed through by means of a sparger2) Cold water is input into the first stage of the reactor by a circulating cooling water tank to keep the temperature of the reaction liquid at 30 ℃, carbon dioxide is introduced for reaction for 1 hour, the temperature is raised to 60 ℃, and carbon dioxide is continuously introduced for reaction for 2 hours. Obtaining viscous liquid CA-TETA containing carbamate after reaction, and obtaining 15.19% of carbon dioxide after weighing calculation; calculated by Thermogravimetric analyzer (TGA) analysisThe carbon dioxide content obtained was 16.86%, i.e. the above viscous liquid contained 16.86% by weight of carbamate. The maximum foaming temperature obtained by Differential scanning thermal card analysis (DSC) was 148.6 ℃.
Synthesis example 2(CA-PEI300)
PEI300(150g) was taken and placed in a 2 liter jacketed glass reactor to mechanically stir the reaction solution and to which carbon dioxide (20 Kg/cm) was introduced by means of a sparger2) Cold water is input into the first stage of the reactor by a circulating cooling water tank to keep the temperature of the reaction liquid at 30 ℃, carbon dioxide is introduced for reaction for 1 hour, the temperature is raised to 60 ℃, and carbon dioxide is continuously introduced for reaction for 2 hours. Obtaining viscous liquid CA-PEI300 containing carbamate after reaction, wherein the amount of carbon dioxide obtained by weighing calculation is 9.98%; the carbon dioxide content was calculated to be 9.78% by TGA analysis, i.e. the above viscous liquid contained 9.78 wt% carbamate. The maximum foaming temperature was 155.7 ℃ as determined by DSC analysis.
Synthesis example 3(CA-TMD)
TMD (150g) was placed in a 2 liter jacketed glass reactor, the reaction solution was mechanically stirred and carbon dioxide (20 Kg/cm) was introduced using a sparger2) Cold water is input into the first stage of the reactor by a circulating cooling water tank to keep the temperature of the reaction liquid at 30 ℃, carbon dioxide is introduced for reaction for 1 hour, the temperature is raised to 60 ℃, and carbon dioxide is continuously introduced for reaction for 2 hours. Obtaining viscous liquid CA-TMD containing carbamate after reaction, and obtaining 14.23% of carbon dioxide after weighing calculation; the carbon dioxide content was calculated by TGA analysis to be 14.23%, i.e. the above viscous liquid contained 14.23% by weight of carbamate. The maximum foaming temperature was 130.2 ℃ as determined by DSC analysis.
Synthesis example 4(CA-BAC)
BAC (150g) was taken out and placed in a 2 liter jacketed glass reactor to mechanically stir the reaction solution and to which carbon dioxide (20 Kg/cm) was passed through by means of a sparger2) Cold water is input into the first stage of the reactor by a circulating cooling water tank to keep the temperature of the reaction liquid at 30 ℃, carbon dioxide is introduced for reaction for 1 hour, the temperature is raised to 60 ℃, and carbon dioxide is continuously introduced for reaction for 2 hours. Obtaining viscous liquid CA-BAC containing carbamate after reaction, and calculating weighingThe amount of the obtained carbon dioxide is 11.96 percent; the carbon dioxide content was 12.67% calculated by TGA analysis, i.e. the above viscous liquid contained 12.67 wt% carbamate. The maximum foaming temperature was 135.7 ℃ as determined by DSC analysis.
Synthesis example 5(CA-mXDA)
mXDA (150g) was placed in a 2 liter jacketed glass reactor, the reaction solution was mechanically stirred and carbon dioxide (20 Kg/cm) was introduced using a sparger2) Cold water is input into the first stage of the reactor by a circulating cooling water tank to keep the temperature of the reaction liquid at 30 ℃, carbon dioxide is introduced for reaction for 1 hour, the temperature is raised to 60 ℃, and carbon dioxide is continuously introduced for reaction for 2 hours. Obtaining viscous liquid CA-mXDA containing carbamate after reaction, and obtaining 12.75% of carbon dioxide after weighing calculation; the carbon dioxide content was calculated to be 13.02% by TGA analysis, i.e. the above viscous liquid contained 13.02% by weight of carbamate. The maximum foaming temperature was 152.3 ℃ as determined by DSC analysis.
Synthesis example 6(CSBO)
Placing Epoxidized soybean oil (150g) and catalyst TBAB (tetrabutyllamonium bromide, 1.5g, 2 wt%) in a reaction tank, introducing CO2(20Kg/cm2) And raising the temperature to 140 ℃, and continuously stirring for reacting for 24 hours to obtain CSBO, so as to obtain1The reaction conversion was 99% by H NMR spectroscopic analysis.
Example 1
CSBO (100 parts by weight) and CA-TETA (36.4 parts by weight, containing 16.86% carbamate, i.e. 6.1 parts by weight carbamate and 30.3 parts by weight TETA) were taken out after being stirred and mixed uniformly and placed in an oven at 130 ℃ for 20 minutes, and the properties of the product were as follows: density 107Kg/m3Tensile strength of 0.11Kgf/cm2Elongation of 24.2% and tear strength of 0.33 Kgf/cm. In this and the following examples, density was measured by ASTM D3574, tensile strength was measured by ASTM D3574, elongation was measured by ASTM D3574, and tear strength was measured by ASTM D3574.
Example 2
Taking CSBO (100 weight portions), CA-TETA (36.4 weight portions, which contains 16.86% carbamate, namely 6.1 weight portionsThe carbamate of (a) was mixed with 30.3 parts by weight of TETA) and with a filler 031DU40 (5% of the total weight of Akzo Nobel, CSBO and CA-TETA) in a stirred state, and after placing in an oven at 130 ℃ for 30 minutes, the carbamate was removed, and the properties of the product were as follows: density 103Kg/m3Tensile strength of 0.15Kgf/cm2Elongation of 36.7% and tear strength of 0.22 Kgf/cm.
Example 3
CSBO (100 parts by weight), CA-TETA (36.4 parts by weight, 16.86% carbamate, 6.1 parts by weight carbamate and 30.3 parts by weight TETA), and a filler 031DU40 (5% of the total weight of Akzo Nobel and CSBO and CA-TETA) were mixed by stirring and mixed uniformly, placed in an oven at 150 ℃ for 30 minutes and then removed, the product having the following properties: density 95Kg/m3Tensile strength of 0.17Kgf/cm2Elongation of 31.8% and tear strength of 0.24 Kgf/cm.
Example 4
CSBO (100 parts by weight), CA-TETA (36.9 parts by weight, containing 16.86% carbamate, i.e., 6.2 parts by weight carbamate and 30.7 parts by weight TETA), epoxy BDGE (1.8 parts by weight), and filler 031DU40 (available from Akzo Nobel, CSBO, CA-TETA, and BDGE, 5% by weight) were mixed uniformly and placed in an oven at 130 ℃ for 30 minutes, and then taken out, and the product had the following properties: density 122Kg/m3Tensile strength of 0.15Kgf/cm2Elongation 38.8%, and tear strength 0.21 Kgf/cm.
Example 5
CSBO (100 parts by weight), CA-TETA (37.8 parts by weight, containing 16.86% carbamate, i.e., 6.4 parts by weight carbamate and 31.4 parts by weight TETA), epoxy BDGE (3.7 parts by weight), and 031DU40 (available from Akzo Nobel, CSBO, CA-TETA, and BDGE) were mixed uniformly and stirred, placed in an oven at 130 ℃ for 30 minutes, and then taken out, and the product had the following properties: density 114Kg/m3Tensile strength of 0.57Kgf/cm2Elongation 39.5%, tear strength 0.45 Kgf/cm.
Example 6
Taking CSBO (100 weight portions), CA-TETA (36.8 weight portions, containing 16.86% carbamate, namely 6.2 weight portions of carbamateThe salt was mixed with 30.6 parts by weight of TETA), epoxy RDGE (2.1 parts by weight), and filler 031DU40 (5% of the total weight of Akzo Nobel, CSBO, CA-TETA, and RDGE) by stirring and mixing, and then placed in an oven at 130 ℃ for 30 minutes and removed, and the product had the following properties: density 106Kg/m3Tensile strength of 0.19Kgf/cm2Elongation 35.5% and tear strength 0.20 Kgf/cm.
Example 7
CSBO (100 parts by weight), CA-TETA (37.6 parts by weight, containing 16.86% carbamate, i.e., 6.3 parts by weight carbamate and 31.3 parts by weight TETA), epoxy RDGE (4.3 parts by weight), and filler 031DU40 (available from Akzo Nobel, CSBO, CA-TETA, and RDGE, 5% by weight) were mixed uniformly and placed in an oven at 130 ℃ for 30 minutes, and then removed, and the product had the following properties: density 97Kg/m3Tensile strength of 0.70Kgf/cm2Elongation of 40.3% and tear strength of 0.36 Kgf/cm.
Example 8
CSBO (100 weight portions), CA-TETA (36.8 weight portions, containing 16.86% carbamate, namely 6.2 weight portions of carbamate and 30.6 weight portions of TETA), epoxy resin DABGE (3.2 weight portions), and filler 031DU40 (purchased from Akzo Nobel, CSBO, CA-TETA, and 5% of total weight of DABGE) are taken, stirred and mixed uniformly, placed in an oven at 130 ℃ for 30 minutes and then taken out, and the product has the following properties: density 96Kg/m3Tensile strength of 0.16Kgf/cm2Elongation 38.3% and tear strength 0.22 Kgf/cm.
Example 9
CSBO (100 weight portions), CA-TETA (37.7 weight portions, containing 16.86% carbamate, namely 6.4 weight portions of carbamate and 31.3 weight portions of TETA), epoxy resin DABGE (6.6 weight portions), and filler 031DU40 (purchased from Akzo Nobel, CSBO, CA-TETA, and 5% of total weight of DABGE) were taken, stirred, mixed uniformly, placed in an oven at 130 ℃ for 30 minutes, and then taken out, and the product had the following properties: density 101Kg/m3Tensile strength of 0.82Kgf/cm2Elongation of 31.1% and tear strength of 0.55 Kgf/cm.
Example 10
Collecting CSBO (100 weight parts) and CA-TETA (36.4 weight parts)Parts of 16.86% carbamate, i.e. 6.1 parts by weight carbamate and 30.3 parts by weight TETA, filler 031DU40 (2.5% of the total weight of akzo nobel, CSBO and CA-TETA), filler 920DU40 (2.5% of the total weight of akzo nobel, CSBO and CA-TETA), were mixed homogeneously and, after placing in an oven at 150 ℃ for 30 minutes, removed, the product had the following properties: density 82Kg/m3Tensile strength of 0.15Kgf/cm2Elongation 32.2%, and tear strength 0.26 Kgf/cm.
Example 11
CSBO (100 parts by weight), CA-TETA (36.4 parts by weight, 16.86% carbamate, 6.1 parts by weight carbamate and 30.3 parts by weight TETA), and filler 920DU40 (2.5% of the total weight of Akzo Nobel, CSBO and CA-TETA) were mixed by stirring and mixed uniformly, placed in an oven at 150 ℃ for 30 minutes and then removed, the product having the following properties: density 157Kg/m3Tensile strength of 0.39Kgf/cm2Elongation 25.1%, and tear strength 0.40 Kgf/cm.
TABLE 1
As is clear from Table 1, the addition of an epoxy resin (as a crosslinking agent) contributes to the improvement of the tensile strength and tear strength of the foam.
Example 12
CSBO (100 weight parts), CA-TETA (18.2 weight parts containing 16.86% carbamate, i.e., 3.1 weight parts carbamate and 15.1 weight parts TETA), filler 031DU40 (2.5% of the total weight of CSBO and CA-TETA), and filler 920DU40 (2.5% of the total weight of CSBO and CA-TETA), were mixed uniformly and stirred, and then placed in an oven at 150 ℃ for 60 minutes, and the product had the following properties: density 92Kg/m3Tensile strength of 0.12Kgf/cm2And the elongation is 75.6%.
Example 13
Taking CSBO (100 weight portions), CA-TETA (72.7 weight portions, which contains 16.86% of carbamate, namely 12.2 weight portions of carbamate and 60.5 weight portionsParts of TETA), filler 031DU40 (2.5% of the total weight of Akzo Nobel, CSBO and CA-TETA), filler 920DU40 (2.5% of the total weight of Akzo Nobel, CSBO and CA-TETA), were mixed homogeneously and after placing in an oven at 150 ℃ for 60 minutes were removed, the product had the following properties: density 80Kg/m3Tensile strength of 0.10Kgf/cm2And the elongation is 94.7%.
Example 14
CSBO (100 parts by weight), CA-TETA (28.8 parts by weight, containing 16.86% carbamate, i.e. 4.8 parts by weight carbamate and 24.0 parts by weight TETA), CA-TMD (7.6 parts by weight, containing 14.23% by weight carbamate, i.e. 1.1 parts by weight carbamate and 6.5 parts by weight TMD), filler 031DU40 (obtained from Akzo Nobel, CSBO, CA-TETA, 2.5% of the total weight of CA-TMD), and filler 920DU40 (obtained from Akzo Nobel, CSBO, CA-TETA, 2.5% of the total weight of CA-TMD) were mixed homogeneously and, after placing in an oven at 150 ℃ for 30 minutes, the product was removed and had the following properties: density 109Kg/m3Tensile strength of 0.31Kgf/cm2Elongation 67.2%, and tear strength 0.53 Kgf/cm.
Example 15
CSBO (100 parts by weight), CA-TETA (28.9 parts by weight containing 16.86% carbamate, i.e., 4.9 parts by weight carbamate and 24.0 parts by weight TETA), CA-BAC (6.8 parts by weight containing 12.67% by weight carbamate, i.e., 0.8 parts by weight carbamate and 6.0 parts by weight BAC), filler 031DU40 (2.5% of the total weight of Akzo Nobel, CSBO, CA-TETA and CA-BAC), and filler 920DU40 (2.5% of the total weight of Akzo Nobel, CSBO, CA-TETA and CA-BAC) were mixed uniformly and stirred, and then placed in an oven at 150 ℃ for 30 minutes and removed, and the product had the following properties: density 112Kg/m3Tensile strength of 0.35Kgf/cm2Elongation of 47.1% and tear strength of 0.68 Kgf/cm.
Example 16
Taking CSBO (100 parts by weight), CA-TETA (28.9 parts by weight containing 16.86% carbamate, i.e. 4.9 parts by weight carbamate and 24.0 parts by weight TETA), CA-PEI300(6.8 parts by weight containing 9.78% by weight carbamate, i.e. 0.7 parts by weight carbamate and 61 part by weight of PEI300), filler 031DU40 (2.5% of the total weight of the filler obtained from Akzo Nobel, CSBO, CA-TETA and CA-PEI300), filler 920DU40 (2.5% of the total weight of the filler obtained from Akzo Nobel, CSBO, CA-TETA and CA-PEI300), after mixing homogeneously and stirring, the mixture is placed in an oven at 150 ℃ for 30 minutes and removed, the product having the following properties: density 118Kg/m3Tensile strength of 0.44Kgf/cm2Elongation 33.9%, and tear strength 0.46 Kgf/cm.
Example 17
CSBO (100 parts by weight), CA-TETA (28.8 parts by weight, containing 16.86% carbamate, i.e. 4.8 parts by weight carbamate and 24.0 parts by weight TETA), CA-mXDA (8.2 parts by weight, containing 13.02% carbamate, i.e. 1.1 parts by weight carbamate and 7.1 parts by weight mXDA), filler 031DU40 (2.5% of the total weight of Akzo Nobel, CSBO, CA-TETA and CA-mXDA), and filler 920DU40 (2.5% of the total weight of Akzo Nobel, CSBO, CA-TETA and CA-mXDA) were mixed homogeneously and placed in an oven at 150 ℃ for 30 minutes before being removed, and the product had the following properties: density 120Kg/m3Tensile strength of 0.47Kgf/cm2Elongation 52.6%, and tear strength 0.51 Kgf/cm.
TABLE 2
As can be seen from Table 2, the tensile strength of the foamed material can be increased and the density of the foamed material can be increased by adjusting the composition of the foaming agent.
Example 18
After uniformly stirring and mixing CDCE (100 parts by weight), CA-TETA (54.6 parts by weight, which contains 16.86% of carbamate, i.e. 9.2 parts by weight of carbamate and 45.4 parts by weight of TETA), a filler 031DU40 (2.5% of the total weight of Akzo Nobel, CDCE and CA-TETA) and a filler 920DU40 (2.5% of the total weight of Akzo Nobel, CDCE and CA-TETA), the mixture was placed in an oven at 150 ℃ for 30 minutes and then taken out, and the product had the following properties: density 139Kg/m3Tensile strength 1.06Kgf/cm2And the elongation is 8.2%.
Example 19
PE300C (100 parts by weight), CA-TETA (59.7 parts by weight, containing 16.86% carbamate, i.e., 10.1 parts by weight carbamate and 49.6 parts by weight TETA), filler 031DU40 (2.5% of the total weight of CA-TETA, available from Akzo Nobel, PE300C), and filler 920DU40 (2.5% of the total weight of CA-TETA, available from Akzo Nobel, PE300C) were taken, mixed uniformly with stirring, placed in an oven at 150 ℃ for 30 minutes, and then removed, and the product had the following properties: density 142Kg/m3Tensile strength of 0.88Kgf/cm2The elongation is 15.1%.
Example 20
RDCE (100 parts by weight), CA-TETA (53.6 parts by weight, 16.86% carbamate, i.e., 9.0 parts by weight carbamate and 44.6 parts by weight TETA), filler 031DU40 (2.5% of the total weight of Akzo Nobel, RDCE and CA-TETA), and filler 920DU40 (2.5% of the total weight of Akzo Nobel, RDCE and CA-TETA) were mixed uniformly and stirred, placed in an oven at 150 ℃ for 30 minutes and then removed, and the product had the following properties: density 138Kg/m3Tensile strength 1.24Kgf/cm2And the elongation is 9.5%.
Example 21
CSBO (100 weight portions), CDCE (28.6 weight portions), CA-TETA (50.3 weight portions containing 16.86% of carbamate, i.e. 8.5 weight portions of carbamate and 41.8 weight portions of TETA), a filler 031DU40 (2.5% of the total weight of Akzo Nobel, CSBO, CDCE and CA-TETA) and a filler 920DU40 (2.5% of the total weight of Akzo Nobel, CSBO, CDCE and CA-TETA) are taken, stirred, mixed uniformly and placed in an oven at 150 ℃ for 30 minutes, and then taken out, and the product has the following properties: density 94Kg/m3Tensile strength of 0.51Kgf/cm2The elongation was 27.4% and the tear strength was 0.45 Kgf/cm.
Example 22
CSBO (100 parts by weight), PE300C (36.1 parts by weight), CA-TETA (50.1 parts by weight containing 16.86% carbamate, i.e., 8.4 parts by weight carbamate and 41.7 parts by weight TETA), filler 031DU40 (available from Akzo Nobel, CSBO, PE300C, 2.5% of the total weight of CA-TETA), and filler 920DU40 (available from Akzo Nobel, CSBO, PE300C, 2.5% of the total weight of CA-TETA) were mixed with stirringAfter uniform mixing, the mixture is placed in an oven at 150 ℃ for 30 minutes and then taken out, and the properties of the product are as follows: density 93Kg/m3Tensile strength of 0.28Kgf/cm2The elongation was 35.9% and the tear strength was 0.26 Kgf/cm.
Example 23
CSBO (100 weight portions), RDCE (25.9 weight portions), CA-TETA (50.2 weight portions containing 16.86% of carbamate, i.e. 8.5 weight portions of carbamate and 41.7 weight portions of TETA), a filler 031DU40 (2.5% of the total weight of Akzo Nobel, CSBO, RDCE and CA-TETA) and a filler 920DU40 (2.5% of the total weight of Akzo Nobel, CSBO, RDCE and CA-TETA) are taken, stirred and mixed uniformly, placed in an oven at 150 ℃ for 30 minutes and then taken out, and the product has the following properties: density 99Kg/m3Tensile strength of 0.56Kgf/cm2The elongation was 25.5% and the tear strength was 0.58 Kgf/cm.
TABLE 3
As is clear from Table 3, the foams of rigid structure cyclic carbonate based compounds (e.g., CDCE, RDCE) have high tensile strength and their hardness properties are suitable for comparative rigid foam 1
CSBO (100 weight portions), TETA (30.4 weight portions), a filler 031DU40 (2.5 percent of the total weight of the CSBO and the TETA) and a filler 920DU40 (2.5 percent of the total weight of the Akzo Nobel, the CSBO and the TETA) are taken, stirred, mixed uniformly and placed in an oven at 150 ℃ for 30 minutes and then taken out, and the product has the following properties: density of 572Kg/m3Tensile strength of 0.77Kgf/cm2The elongation was 28.9% and the tear strength was 0.54 Kgf/cm. The above product is clearly not foamed.
Comparative example 2
CSBO (100 weight portions), TETA (15.3 weight portions), TMD (16.5), filler 031DU40 (purchased from Akzo Nobel, CSBO, TETA, and 2.5% of the total weight of TMD), filler 920DU40 (purchased from Akzo Nobel, CSBO, TETA, and 2.5% of the total weight of TMD) were stirred and mixed uniformly, placed in an oven at 150 ℃ for 30 minutes and then taken out, and the product had the following properties: density 601Kg/m3Tensile strength 1.49Kgf/cm2The elongation was 56.3% and the tear strength was 0.75 Kgf/cm. The above product is clearly not foamed.
TABLE 4
As can be seen from Table 4, no low-density foamed product could be obtained without using carbamate.
Comparative example 3
CSBO (100 weight portions), CA-TETA (36.4 weight portions) and a filler 031DU40 (5 percent of the total weight of the CSBO and CA-TETA purchased from Akzo Nobel) are taken to be stirred and mixed evenly, and then the mixture is taken out after being placed in an oven at 100 ℃ for 30 minutes, and the product has the following properties: the density is 860Kg/m3. The above product is clearly not foamed.
Comparative example 4
CSBO (100 parts by weight), CA-TETA (36.4 parts by weight), and a filler 031DU40 (5% of the total weight of the mixture of CSBO and CA-TETA, available from Akzo Nobel) were mixed by stirring, placed in an oven at 170 ℃ for 30 minutes, and then removed, the product having the following properties: density 320Kg/m3. The above product is severely broken. It is understood from comparative examples 3 and 4 that the temperature of the heated foaming composition is too high or too low, and the properties of the foamed product are deteriorated.
Although the present disclosure has been described with reference to a number of preferred embodiments, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the disclosure, and the scope of the disclosure should be limited only by the appended claims.
Claims (12)
1. A foaming composition comprising:
100 parts by weight of a cyclic carbonate-based compound; and
a blowing agent,
wherein the blowing agent comprises:
3 to 13 parts by weight of a carbamate; and
15 to 65 parts by weight of an amino compound.
2. The foaming composition of claim 1, wherein the cyclic carbonate-based compound has the structure:
wherein n is an integer from 1 to 6; and R1Is aliphatic compound, alicyclic compound, aromatic compound, alkyl substituted aromatic compound, polyether oligomer, polyester oligomer or the combination of the above compounds; and
R2is H, an aliphatic compound containing a cyclic carbonate group, or a combination of the above.
3. The foaming composition of claim 1, wherein said carbamate is formed from the reaction of an amino compound and carbon dioxide, and said carbamate has the structure:
wherein R is3Is C1～C12Polyether amines, alkyl amines, cycloalkyl amines, aryl amines, or combinations thereof.
4. The foaming composition of claim 1, wherein the amino compound comprises triethylene tetramine, trimethyl hexamethylene diamine, polyethylene imine, bis-methyl amine cyclohexane, m-xylylenediamine, poly (propylene ether amine) diamine, polyether amine, ethylene diamine, or combinations thereof.
5. The foaming composition of claim 1, further comprising 0.1 to 10 parts by weight of an epoxy compound having the structure:
wherein m is an integer from 1 to 6;
R4is aliphatic compound, alicyclic compound, aromatic compound, alkyl substituted aromatic compound, polyether oligomer, polyester oligomer or the combination of the above compounds; and
R5is H, an aliphatic compound containing a cyclic carbonate group, or a combination of the above.
6. The foaming composition of claim 1, further comprising 2 to 10 parts by weight of a filler, and the filler comprises hollow microbeads, vermiculite, or a combination thereof.
7. A method of forming a foamed material, comprising:
mixing 100 parts by weight of a cyclic carbonate-based compound with a blowing agent to form a foaming composition, wherein the blowing agent comprises 3 to 13 parts by weight of a carbamate salt, and 15 to 65 parts by weight of an amino compound; and
heating the foaming composition to 100 ℃ to 170 ℃ to decompose the carbamate salt into carbon dioxide and an amino compound, and the amino compound reacts with the cyclic carbonate-based compound to form a foamed material.
8. The method of forming a foamed material according to claim 7, wherein the cyclic carbonate-based compound has a structure of:
wherein n is an integer from 1 to 6; and R1Is aliphatic compound, alicyclic compound, aromatic compound, alkyl substituted aromatic compound, polyether oligomer, polyester oligomer or the combination of the above compounds; and
R2is H, an aliphatic compound containing a cyclic carbonate group, or a combination of the above.
9. The method of claim 7, wherein the carbamate is formed by reacting an amino compound with carbon dioxide, and the carbamate is:
wherein R is3Is C1～C12Polyether amines, alkyl amines, cycloalkyl amines, aryl amines, or combinations thereof.
10. The method of claim 7, wherein the amino compound comprises triethylene tetramine, trimethyl hexamethylene diamine, polyethylene imine, bis-methyl amine cyclohexane, m-xylylenediamine, poly (propylene ether amine) diamine, polyether amine, ethylene diamine, or combinations thereof.
11. The method of claim 7, wherein the foaming composition further comprises 0.1 to 10 parts by weight of an epoxy compound, the epoxy compound having the structure:
wherein m is an integer from 1 to 6;
R4is aliphatic compound, alicyclic compound, aromatic compound, alkyl substituted aromatic compound, polyether oligomer, polyester oligomer or the combination of the above compounds; and
R5is H, an aliphatic compound containing a cyclic carbonate group, or a combination of the above.
12. The method of claim 7, wherein the foaming composition further comprises 2 to 10 parts by weight of a filler, and the filler comprises hollow micro beads, vermiculite, or a combination thereof.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1334827A (en) * | 1998-12-15 | 2002-02-06 | 伊斯曼化学公司 | Powder coatings from cyclic carbonate functional polymers and amine carbamate salts |
| US20170218124A1 (en) * | 2016-01-29 | 2017-08-03 | Faurecia Interieur Industrie | Non isocyanate polyurethane foams |
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2019
- 2019-12-31 CN CN201911403060.7A patent/CN113121863A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1334827A (en) * | 1998-12-15 | 2002-02-06 | 伊斯曼化学公司 | Powder coatings from cyclic carbonate functional polymers and amine carbamate salts |
| US20170218124A1 (en) * | 2016-01-29 | 2017-08-03 | Faurecia Interieur Industrie | Non isocyanate polyurethane foams |
Non-Patent Citations (1)
| Title |
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| 李振荣等: "大豆油五元环状碳酸酯与双酚A环氧树脂共混体系的研究", 《化工新型材料》 * |
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