CN103030965B - Method for preparing castor-oil-based flame-retardant polyurethane elastomer - Google Patents
Method for preparing castor-oil-based flame-retardant polyurethane elastomer Download PDFInfo
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- 239000004359 castor oil Substances 0.000 title claims abstract description 37
- 235000019438 castor oil Nutrition 0.000 title claims abstract description 37
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 title claims abstract description 37
- 239000003063 flame retardant Substances 0.000 title claims abstract description 29
- 229920003225 polyurethane elastomer Polymers 0.000 title claims abstract description 17
- 229960001777 castor oil Drugs 0.000 title abstract description 28
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title abstract description 10
- 238000000034 method Methods 0.000 title abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 238000007259 addition reaction Methods 0.000 claims abstract description 7
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 claims description 28
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 claims description 17
- 235000004443 Ricinus communis Nutrition 0.000 claims description 15
- 229920002635 polyurethane Polymers 0.000 claims description 14
- 239000004814 polyurethane Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229920001971 elastomer Polymers 0.000 claims description 9
- 239000000806 elastomer Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 4
- 125000005456 glyceride group Chemical group 0.000 claims description 2
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 229910002804 graphite Inorganic materials 0.000 abstract description 3
- 239000010439 graphite Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 229920005862 polyol Polymers 0.000 abstract description 3
- 150000003077 polyols Chemical class 0.000 abstract description 3
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 1
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- 229920000570 polyether Polymers 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 240000000528 Ricinus communis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 230000002687 intercalation Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- -1 makeup Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention discloses a method for preparing a castor-oil-based flame-retardant polyurethane elastomer and belongs to the technical field of polymers synthetic chemistry. The method comprises the following steps of: by using cheap and renewable castor oil as the raw material, performing double-bond addition reaction on the castor oil and a fire retardant DOPO at a temperature of 80 to 160 DEG C to obtain modified castor oil; and performing reaction on the modified castor oil, which replaces polyether polyol, and diisocyanate, adding a certain quantity of expansible graphite with specification of 200 to 500 meshes to prepare the flame-retardant polyurethane elastomer. The polyurethane elastomer prepared by the method has the characteristics of low cost, excellent flame-retardant effect and the like.
Description
Technical field
The invention belongs to polymer synthetic chemistry technical field, relate to a kind of fire-retardant polyurethane based on castor oil method for producing elastomers: the method is by the reproducible Viscotrol C of cheapness is carried out to modification, taking modified castor oil as raw material, react with polyisocyanates and prepare castor oil-base flame resistance polyurethane elastomer again.
Background technology
Because the continuous reinforcement renewable resources of the worsening shortages of petroleum resources and people's environmental consciousness is produced biomaterial, industrial chemicals and fuel and more and more attract people's attention.The vegetables oil of hydroxyl or hydroxylated vegetables oil as polyvalent alcohol for the preparation of the urethane requirement that meets environment protection completely become a kind of novel high polymer material of showing up prominently in China in recent years.
Viscotrol C, as a kind of natural polyol, has typical unsaturated fatty acids triglyceride structure.Be widely used in the industry such as tackiness agent, coating, makeup, ink, urethane.As the green renewable resources of one, castor oil-base compound has potential biodegradability. and Viscotrol C is often used as polyol component, generate polyurethane elastomer, semi-rigid foam or prepare interpenetrating polymer networks with isocyanate reaction, appropriate Viscotrol C can improve tensile strength, water tolerance and the thermotolerance of glued membrane.
Viscotrol C is one of ten large oil plants and four large unedible oil crops in the world, is a kind of tri-glyceride of natural acid, and the main component in lipid acid is ricinolic acid: CH
3(CH
2)
5cH (OH)=CH (CH
2)
7cOOH accounts for 90%, is secondly oleic acid, linolic acid, is unique vegetables oil that contains hydroxyl in vegetables oil.Have this Witepsol W-S 55 of 75% left and right containing three castor-oil plant acyl groups, remaining triglyceride is mainly containing two castor-oil plant acyl groups and other long-chain fat acyl group.The hydroxyl average functionality of Viscotrol C is 2.7 left and right, belongs to nondrying oil.
Viscotrol C main component chemical formula is as follows
The annual production of China's Viscotrol C occupies the 3rd, the world, source is abundant, polyurethane based on castor oil taking natural reproducible and cheap and Viscotrol C as raw material, introduce hydroxyl by modification, replace other petroleum type polyvalent alcohols, synthesis of polyurethane, can alleviate the shortage of petroleum resources, reduces the cost of urethane.
Polyurethane elastomer, with its good physical and mechanical property, acoustical behavior, electric property and chemical resistance, is used widely.Use very generally in departments such as furniture, bed accessory, transport, refrigeration, building, thermal insulation especially, become one of indispensable material.But in recent decades, the fire failure of polyurethane material frequently occurs, and the safety issue of material becomes more and more important.Its inflammableness limits its application to a certain extent.
DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) is a kind of important organophosphorous fire retardant intermediate, is subject in recent years extensive concern.Different from additive flame retardant, in DOPO molecule, contain P-H key, can carry out addition reaction with unsaturated link(age), carbonyl, epoxy group(ing) etc., generate various DOPO derivatives.Response type DOPO based flameproofing can have been avoided the migration of fire retardant, can well improve fire retardant utilising efficiency.
Expansible black lead (EG) can be described as again compound between graphite layers.EG is decomposed and is started to expand by intercalation compound 200 DEG C of left and right, and 900 DEG C of left and right reach maximum value, and expansion multiplying power is 280 times.Graphite after expansion becomes by original flakey " worm " shape that density is very low, has formed a thermal insulation, oxygen barrier layer.It not only can with the effect of phosphorus flame retardant cooperative flame retardant, it can also effectively play the effect of anti-drippage in expanded by heating process.
Summary of the invention
One of object of the present invention is to provide a kind of fire-retardant polyurethane based on castor oil method for producing elastomers.
Technical scheme of the present invention is as follows:
A kind of fire-retardant polyurethane based on castor oil method for producing elastomers, carries out according to following step:
(1) there are two key addition reactions at 80～160 DEG C with fire retardant DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) in Viscotrol C, and reaction 4-8h makes modified castor oil;
(2) by above-mentioned modified castor oil, at 100～140 DEG C, vacuumize the 2～4h that dewaters, for subsequent use;
(3) dewater post-modification Viscotrol C and vulcabond, mix in the ratio of R=CNO/OH=2～4 (mol ratio), in 100 parts of mixtures, add 200～500 order expansible black leads of 3～8 parts, stir, be then poured into preheating and scribble in the flat plate mold of releasing agent, be slowly warming up to 50～100 DEG C, after isothermal reaction 10～18h, pressurization 1～10MPa cure and demold; At room temperature vulcanize 7d, obtain castor oil-base flame resistance polyurethane elastomer.
Viscotrol C described in above-mentioned steps (1) is pure Viscotrol C or industrial one-level Viscotrol C.Industry one-level Viscotrol C is the glyceride type compound of octadecenoic acid; Wherein pure Viscotrol C content accounts for 80%.
In above-mentioned steps (1), DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) structural formula is:
In above-mentioned steps (1), the mass ratio of Viscotrol C and DOPO is 1:0.6.
In above-mentioned steps (1), preferably temperature is 100～140 DEG C.
In above-mentioned steps (3), the preferred temperature of temperature of reaction is 60～80 DEG C.
In above-mentioned steps (3), modified castor oil and vulcabond, mix in the ratio of R=CNO/OH=2～4 (mol ratio), preferably R=2.5～3.5.
Preferably 4 parts～6 parts of the additions of the middle expansible black lead of above-mentioned steps (3).
Castor oil-base flame retardant polyurethane prepared by the present invention, adopts cheap renewable resources---Viscotrol C be that raw material is prepared polyurethane based on castor oil, add part expansible black lead as anti-dripping agent, can make the flame retardant resistance of goods can reach V0 level.
Embodiment:
Below in conjunction with embodiment, the present invention is further illustrated, but do not limit the present invention.Except as otherwise noted, all umbers and per-cent is all in mass in an embodiment.
Embodiment 1
Prepare modified castor oil base.In reactor, add 100 parts of Viscotrol C, with 20 parts of fire retardant DOPO, two key addition reactions occur at 100 DEG C, after reaction 4h, make modified castor oil.Modified castor oil, at 100 DEG C, vacuumizes the 2h that dewaters, for subsequent use.
Prepare the method for castor oil-base flame resistance polyurethane elastomer.In the above-mentioned modified castor oil preparing, add R=CNO/OH=2.5 (mol ratio) liquefaction diphenylmethanediisocyanate, ratio is mixed, in 100 parts of mixtures, add the 200 order expansible black leads of 4 parts, stir, be then poured into preheating and scribble in the flat plate mold of releasing agent, at 60 DEG C, react after 18h pressurization 10MPa cure and demold.At room temperature vulcanize 7d, obtain castor oil-base flame resistance polyurethane elastomer.
Embodiment 2
Prepare modified castor oil base.In reactor, add 100 parts of Viscotrol C, with 60 parts of fire retardant DOPO, two key addition reactions occurring at 140 DEG C, after reaction 6h, make modified castor oil.Modified castor oil, at 140 DEG C, vacuumizes the 3h that dewaters, for subsequent use.
Prepare the method for castor oil-base flame resistance polyurethane elastomer.In the above-mentioned modified castor oil preparing, add R=CNO/OH=3.5 (mol ratio) liquefaction diphenylmethanediisocyanate, ratio is mixed, in 100 parts of mixtures, add the 400 order expansible black leads of 6 parts, stir, be then poured into preheating and scribble in the flat plate mold of releasing agent, at 80 DEG C, react after 10h pressurization 5MPa cure and demold.At room temperature vulcanize 7d, obtain castor oil-base flame resistance polyurethane elastomer.
Embodiment 3
Prepare modified castor oil base.In reactor, add 100 parts of Viscotrol C, with 40 parts of fire retardant DOPO, two key addition reactions occurring at 120 DEG C, after reaction 8h, make modified castor oil.Modified castor oil, at 120 DEG C, vacuumizes the 4h that dewaters, for subsequent use.
Prepare the method for castor oil-base flame resistance polyurethane elastomer.In the above-mentioned modified castor oil preparing, add R=CNO/OH=3 (mol ratio) tolylene diisocyanate, ratio is mixed, in 100 parts of mixtures, add the 500 order expansible black leads of 5 parts, stir, be then poured into preheating and scribble in the flat plate mold of releasing agent, at 70 DEG C, react after 6h pressurization 1MPa cure and demold.At room temperature vulcanize 7d, obtain castor oil-base flame resistance polyurethane elastomer.
Castor oil-base flame resistance polyurethane elastomer prepared by above-mentioned example, oxygen index LOI measures according to GB/T2406-1993, and vertical combustion is measured according to GB8333-1987
| Numbering | LOI | UL-94 |
| Example one | 26.4 | V1 |
| Example two | 32.4 | V0 |
| Example three | 29.1 | V0 |
As can be seen from the above table, 20 parts of the interpolations of example one modified castor oil DOPO, in urethane, expansible black lead adds 4 parts, and fire-retardant rank can reach V1 level.And along with the increase of the addition of DOPO, the oxygen index (LOI) of urethane improves thereupon, flame retardant rating is also brought up to V0 from V1.
Claims (6)
1. a fire-retardant polyurethane based on castor oil method for producing elastomers, is characterized in that carrying out according to following step:
(1) there are two key addition reactions at 80～160 DEG C with fire retardant 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide in Viscotrol C, and reaction 4-8h makes modified castor oil;
(2) by above-mentioned modified castor oil, at 100～140 DEG C, vacuumize the 2～4h that dewaters, for subsequent use;
(3) dewater post-modification Viscotrol C and vulcabond, the ratio of R=2～4 is mixed in molar ratio, wherein R=CNO/OH, in 100 parts of mixtures, add 200～500 order expansible black leads of 3～8 parts, stir, then be poured into preheating and scribble in the flat plate mold of releasing agent, slowly be warming up to 50～100 DEG C, after isothermal reaction 10～18h, pressurization 1～10MPa cure and demold; At room temperature vulcanize 7d, obtain castor oil-base flame resistance polyurethane elastomer.
2. the fire-retardant polyurethane based on castor oil method for producing elastomers of one according to claim 1, is characterized in that Viscotrol C described in step (1) is pure Viscotrol C or industrial one-level Viscotrol C; The glyceride type compound that wherein industrial one-level Viscotrol C is octadecenoic acid, wherein pure Viscotrol C content accounts for 80%; The mass ratio of Viscotrol C and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide is 1:0.6.
3. the fire-retardant polyurethane based on castor oil method for producing elastomers of one according to claim 1, is characterized in that in step (1), temperature is 100～140 DEG C.
4. the fire-retardant polyurethane based on castor oil method for producing elastomers of one according to claim 1, is characterized in that in step (3), temperature of reaction is 60～80 DEG C.
5. the fire-retardant polyurethane based on castor oil method for producing elastomers of one according to claim 1, is characterized in that modified castor oil and vulcabond, in molar ratio R=2.5～3.5 in step (3).
6. the fire-retardant polyurethane based on castor oil method for producing elastomers of one according to claim 1, is characterized in that the addition of expansible black lead in step (3) is 4 parts～6 parts.
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| CN103319675B (en) * | 2013-05-24 | 2015-07-29 | 中国林业科学研究院林产化学工业研究所 | Castor oil-base flame-proof polyol composition and method of making the same and application |
| CN103951845B (en) * | 2014-04-02 | 2017-08-01 | 合肥杰事杰新材料股份有限公司 | A kind of fullerene as composition flame-retardant anti-dropping agent purposes |
| CN103923348A (en) * | 2014-04-02 | 2014-07-16 | 合肥杰事杰新材料股份有限公司 | Application of graphene as composition flame-retardant anti-dripping agent |
| CN107057036B (en) * | 2017-04-05 | 2019-11-12 | 福建师范大学泉港石化研究院 | A kind of side chain cross-linking flame-retardant can repair the synthetic method of polyurethane |
| CN109354668B (en) * | 2018-09-11 | 2021-12-10 | 东莞市吉鑫高分子科技有限公司 | High-flame-retardant thermoplastic polyurethane elastomer and preparation method thereof |
| CN110423443B (en) * | 2019-08-20 | 2021-06-29 | 湖南工业大学 | Biomass-based high-toughness flame-retardant plate |
| CN114380975B (en) * | 2022-03-07 | 2023-06-13 | 大连理工大学 | Flame-retardant polyurethane and preparation method thereof |
| CN117343270A (en) * | 2023-12-05 | 2024-01-05 | 广州艾科新材料股份有限公司 | Soft polyurethane foam material and preparation method thereof |
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| CN101463122A (en) * | 2009-01-04 | 2009-06-24 | 上海世鹏聚氨酯科技发展有限公司 | Fiber reinforced halogen-free flame-retardant environment friendly energy-saving type intermittent construction heat preserving composite board material |
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