CN106432332A - 一种含磷氮丙烯酸酯及其共聚物核壳粒子的制备方法 - Google Patents
一种含磷氮丙烯酸酯及其共聚物核壳粒子的制备方法 Download PDFInfo
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- CN106432332A CN106432332A CN201610814079.0A CN201610814079A CN106432332A CN 106432332 A CN106432332 A CN 106432332A CN 201610814079 A CN201610814079 A CN 201610814079A CN 106432332 A CN106432332 A CN 106432332A
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- phosphorus
- acrylate
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- nitrogen containing
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- 239000011258 core-shell material Substances 0.000 title claims abstract description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical group [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 32
- 239000002245 particle Substances 0.000 title claims abstract description 29
- 229920001577 copolymer Chemical group 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract description 9
- 229910052698 phosphorus Inorganic materials 0.000 title abstract description 9
- 239000011574 phosphorus Substances 0.000 title abstract description 9
- 229920000058 polyacrylate Polymers 0.000 title abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title abstract 14
- 229910052757 nitrogen Inorganic materials 0.000 title abstract 7
- 239000000178 monomer Substances 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- YUWBVKYVJWNVLE-UHFFFAOYSA-N [N].[P] Chemical compound [N].[P] YUWBVKYVJWNVLE-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000000839 emulsion Substances 0.000 claims description 10
- 238000010792 warming Methods 0.000 claims description 9
- -1 Methyl methacrylate Ester Chemical class 0.000 claims description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- 239000012153 distilled water Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 abstract description 13
- 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 abstract description 7
- 239000004609 Impact Modifier Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000007334 copolymerization reaction Methods 0.000 abstract description 4
- 238000010556 emulsion polymerization method Methods 0.000 abstract description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 3
- 239000011230 binding agent Substances 0.000 abstract description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 238000004079 fireproofing Methods 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 2
- 0 *C*=CC(N)=C1CCC1 Chemical compound *C*=CC(N)=C1CCC1 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4419—Amides of aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4434—Amides thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4438—Ester with hydroxyalkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F275/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers containing phosphorus, selenium, tellurium or a metal as defined in group C08F30/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Graft Or Block Polymers (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
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CN201610814079.0A CN106432332B (zh) | 2016-09-12 | 2016-09-12 | 一种含磷氮丙烯酸酯及其共聚物核壳粒子的制备方法 |
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CN201610814079.0A CN106432332B (zh) | 2016-09-12 | 2016-09-12 | 一种含磷氮丙烯酸酯及其共聚物核壳粒子的制备方法 |
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CN106432332A true CN106432332A (zh) | 2017-02-22 |
CN106432332B CN106432332B (zh) | 2018-10-26 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112467120A (zh) * | 2020-12-01 | 2021-03-09 | 桐乡市华璟科技有限公司 | 一种氮磷掺杂多孔碳包覆二氧化锰的负极材料的制备方法 |
CN114292368A (zh) * | 2022-01-26 | 2022-04-08 | 华北理工大学 | 一种有机硅-含磷丙烯酸酯核壳增韧阻燃剂及其制备方法 |
KR20220117974A (ko) * | 2021-02-18 | 2022-08-25 | 경기대학교 산학협력단 | 유기계 난연성 화합물용 조성물 및 이의 제조방법 |
KR20220160137A (ko) * | 2021-05-26 | 2022-12-06 | 경기대학교 산학협력단 | 유기계 난연성 화합물 및 이의 제조방법 |
Citations (3)
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---|---|---|---|---|
SU10663A1 (ru) * | 1928-04-23 | 1929-07-31 | Е.Г. Ефремов | Устройство дл измерени малых смещений пучка параллельных лучей |
SU1142487A1 (ru) * | 1983-06-15 | 1985-02-28 | Волгоградский Ордена Трудового Красного Знамени Политехнический Институт | Резинова смесь на основе этиленпропилендиенового каучука |
CN101497630A (zh) * | 2009-03-09 | 2009-08-05 | 安徽恒远化工有限公司 | 含磷丙烯酸酯单体及超支化聚合物阻燃剂及其制备方法 |
-
2016
- 2016-09-12 CN CN201610814079.0A patent/CN106432332B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU10663A1 (ru) * | 1928-04-23 | 1929-07-31 | Е.Г. Ефремов | Устройство дл измерени малых смещений пучка параллельных лучей |
SU1142487A1 (ru) * | 1983-06-15 | 1985-02-28 | Волгоградский Ордена Трудового Красного Знамени Политехнический Институт | Резинова смесь на основе этиленпропилендиенового каучука |
CN101497630A (zh) * | 2009-03-09 | 2009-08-05 | 安徽恒远化工有限公司 | 含磷丙烯酸酯单体及超支化聚合物阻燃剂及其制备方法 |
Non-Patent Citations (3)
Title |
---|
K. KOKKLIN ET AL: "Grafting of Phosphonate Monomer onto Natural Rubber Latexes via Emulsion Polymerization", 《FUNCTIONALIZED AND SENSING MATERIALS》 * |
KIM, MOONSUK ET AL: "Phosphonamidates as thermally latent anionic initiators of glycidyl phenyl ether: substituent effect on the initiator activity", 《MACROMOLECULES》 * |
甘孟瑜等: "核壳结构丙烯酸酯乳液的合成及性能研究", 《涂料工业》 * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112467120A (zh) * | 2020-12-01 | 2021-03-09 | 桐乡市华璟科技有限公司 | 一种氮磷掺杂多孔碳包覆二氧化锰的负极材料的制备方法 |
KR20220117974A (ko) * | 2021-02-18 | 2022-08-25 | 경기대학교 산학협력단 | 유기계 난연성 화합물용 조성물 및 이의 제조방법 |
KR102600082B1 (ko) * | 2021-02-18 | 2023-11-07 | 경기대학교 산학협력단 | 유기계 난연성 화합물용 조성물 및 이의 제조방법 |
KR20220160137A (ko) * | 2021-05-26 | 2022-12-06 | 경기대학교 산학협력단 | 유기계 난연성 화합물 및 이의 제조방법 |
KR102678187B1 (ko) * | 2021-05-26 | 2024-06-25 | 경기대학교 산학협력단 | 유기계 난연성 화합물 및 이의 제조방법 |
CN114292368A (zh) * | 2022-01-26 | 2022-04-08 | 华北理工大学 | 一种有机硅-含磷丙烯酸酯核壳增韧阻燃剂及其制备方法 |
CN114292368B (zh) * | 2022-01-26 | 2023-04-11 | 华北理工大学 | 一种有机硅-含磷丙烯酸酯核壳增韧阻燃剂及其制备方法 |
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