ES2295586T3 - Procedimiento de produccion para producto de adicion de oxido de alquileno y mezcla de cemento que lo contiene. - Google Patents
Procedimiento de produccion para producto de adicion de oxido de alquileno y mezcla de cemento que lo contiene. Download PDFInfo
- Publication number
- ES2295586T3 ES2295586T3 ES03728021T ES03728021T ES2295586T3 ES 2295586 T3 ES2295586 T3 ES 2295586T3 ES 03728021 T ES03728021 T ES 03728021T ES 03728021 T ES03728021 T ES 03728021T ES 2295586 T3 ES2295586 T3 ES 2295586T3
- Authority
- ES
- Spain
- Prior art keywords
- alkylene oxide
- meth
- reaction
- addition product
- favorably
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 83
- 239000004568 cement Substances 0.000 title claims description 81
- 238000000034 method Methods 0.000 title claims description 74
- 239000000203 mixture Substances 0.000 title claims description 46
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 275
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 115
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 75
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 67
- 238000006243 chemical reaction Methods 0.000 claims description 160
- 238000005886 esterification reaction Methods 0.000 claims description 146
- 238000006116 polymerization reaction Methods 0.000 claims description 114
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 82
- 239000000178 monomer Substances 0.000 claims description 74
- -1 acrylate ester Chemical class 0.000 claims description 60
- 229920001577 copolymer Polymers 0.000 claims description 50
- 150000002148 esters Chemical class 0.000 claims description 37
- 229920006243 acrylic copolymer Polymers 0.000 claims description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 31
- 238000005809 transesterification reaction Methods 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 21
- 125000005907 alkyl ester group Chemical group 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 238000007259 addition reaction Methods 0.000 abstract description 10
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- 230000002349 favourable effect Effects 0.000 description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000007864 aqueous solution Substances 0.000 description 35
- 150000003839 salts Chemical class 0.000 description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 32
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- 239000002270 dispersing agent Substances 0.000 description 20
- 229920001223 polyethylene glycol Polymers 0.000 description 19
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 17
- 238000006386 neutralization reaction Methods 0.000 description 17
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- 125000005702 oxyalkylene group Chemical group 0.000 description 13
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 230000007062 hydrolysis Effects 0.000 description 12
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- 230000015572 biosynthetic process Effects 0.000 description 11
- 150000005690 diesters Chemical class 0.000 description 11
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 10
- 238000010533 azeotropic distillation Methods 0.000 description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
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- 239000012295 chemical reaction liquid Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 238000005342 ion exchange Methods 0.000 description 9
- 229940124024 weight reducing agent Drugs 0.000 description 9
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
- 229950000688 phenothiazine Drugs 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 238000004811 liquid chromatography Methods 0.000 description 7
- 238000007717 redox polymerization reaction Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- 201000005569 Gout Diseases 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
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- 150000002978 peroxides Chemical class 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- ICQFAQGXJAVDED-UHFFFAOYSA-N benzene-1,4-diol;4-(methylamino)phenol Chemical compound OC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ICQFAQGXJAVDED-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
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- 125000003827 glycol group Chemical group 0.000 description 4
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- 239000000377 silicon dioxide Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- FYRRWGUSDSVKRL-UHFFFAOYSA-N 2-methyl-4-(3-methylbut-3-enoxy)but-1-ene Chemical compound CC(=C)CCOCCC(C)=C FYRRWGUSDSVKRL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 2
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- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- SIGUVTURIMRFDD-UHFFFAOYSA-M sodium dioxidophosphanium Chemical compound [Na+].[O-][PH2]=O SIGUVTURIMRFDD-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- UCWBKJOCRGQBNW-UHFFFAOYSA-M sodium;hydroxymethanesulfinate;dihydrate Chemical compound O.O.[Na+].OCS([O-])=O UCWBKJOCRGQBNW-UHFFFAOYSA-M 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2696—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the process or apparatus used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002146663 | 2002-05-21 | ||
| JP2002-146663 | 2002-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2295586T3 true ES2295586T3 (es) | 2008-04-16 |
Family
ID=29545145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03728021T Expired - Lifetime ES2295586T3 (es) | 2002-05-21 | 2003-05-02 | Procedimiento de produccion para producto de adicion de oxido de alquileno y mezcla de cemento que lo contiene. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7402644B2 (enExample) |
| EP (1) | EP1507815B1 (enExample) |
| JP (2) | JP5084102B2 (enExample) |
| DE (1) | DE60318431T2 (enExample) |
| ES (1) | ES2295586T3 (enExample) |
| WO (1) | WO2003097716A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10237286A1 (de) * | 2002-08-14 | 2004-02-26 | Degussa Construction Chemicals Gmbh | Verwendung von Blockcopolymeren als Dilpergiermittel für wässrige Feststoff-Suspensionen |
| US7875114B2 (en) * | 2005-06-14 | 2011-01-25 | United States Gypsum Company | Foamed slurry and building panel made therefrom |
| JP4918336B2 (ja) * | 2006-11-13 | 2012-04-18 | 花王株式会社 | アルキレンオキシド付加物の製造方法 |
| WO2008126909A1 (en) | 2007-04-05 | 2008-10-23 | Nippon Shokubai Co., Ltd. | Production method of unsaturated (poly)alkylene glycol ether monomer and production method of (poly)alkylene glycol chain-containing polymer |
| JP5426090B2 (ja) * | 2007-12-26 | 2014-02-26 | 株式会社日本触媒 | （ポリ）アルキレングリコール鎖を有する重合体の製造方法 |
| US20100288167A1 (en) * | 2008-02-01 | 2010-11-18 | Wurm David B | Low diol content monofunctional alkoxypolyalkylene glycols and process for producing them |
| JP5398244B2 (ja) * | 2008-12-05 | 2014-01-29 | 株式会社日本触媒 | ポリオキシアルキレン化合物の製法 |
| ATE545673T1 (de) | 2009-06-18 | 2012-03-15 | Basf Se | Verfahren zur herstellung von monohydroxypolyalkylenoxiden |
| JP2011032398A (ja) * | 2009-08-04 | 2011-02-17 | Kao Corp | ノニオン界面活性剤の製造方法 |
| US8586687B2 (en) * | 2010-12-17 | 2013-11-19 | Nippon Shokubai Co., Ltd. | Polyalkylene glycol-based polymer and process for producing the same |
| US9505880B2 (en) * | 2013-06-04 | 2016-11-29 | Corning Incorporated | Synthesis of polyfunctional polyol acrylates |
| US11584932B2 (en) | 2016-11-01 | 2023-02-21 | The Research Foundation For The State University Of New York | 5-halouracil-modified microRNAs and their use in the treatment of cancer |
| JP7363025B2 (ja) * | 2018-11-30 | 2023-10-18 | 株式会社レゾナック | （ポリ）アルキレングリコール系（メタ）アクリレートの製造方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5410399A (en) * | 1977-06-24 | 1979-01-25 | Nippon Oil & Fats Co Ltd | Preparation of polyalkylene glycol derivative |
| JPS60199031A (ja) * | 1984-03-23 | 1985-10-08 | Asahi Glass Co Ltd | ポリエ−テル類の製法 |
| JPH07113060B2 (ja) * | 1988-02-09 | 1995-12-06 | 日本ペイント株式会社 | ポリエーテルポリオールの製法 |
| US5002678A (en) | 1990-06-29 | 1991-03-26 | Olin Corporation | Lubricants for heat transfer fluids |
| JPH08109254A (ja) * | 1994-10-11 | 1996-04-30 | Dai Ichi Kogyo Seiyaku Co Ltd | ポリエーテルの製造方法 |
| KR100247527B1 (ko) * | 1996-04-03 | 2000-03-15 | 겐지 아이다 | 시멘트분산방법및시멘트조성물 |
| JP3327809B2 (ja) | 1996-04-03 | 2002-09-24 | 株式会社日本触媒 | セメント分散剤、セメントの分散方法およびセメント組成物 |
| US6174980B1 (en) * | 1996-12-26 | 2001-01-16 | Nippon Shokubai Co., Ltd. | Cement dispersant, method for producing polycarboxylic acid for cement dispersant and cement composition |
| JP3884548B2 (ja) | 1996-12-26 | 2007-02-21 | 株式会社日本触媒 | セメント分散剤、セメント分散剤用ポリカルボン酸の製造方法およびセメント組成物 |
| US6166112A (en) | 1997-03-10 | 2000-12-26 | Nippon Shokubai Co., Ltd. | Cement admixture and cement composition |
| JP3285820B2 (ja) | 1997-06-10 | 2002-05-27 | 株式会社日本触媒 | ポリカルボン酸の製造方法 |
| JP4385440B2 (ja) | 1999-06-08 | 2009-12-16 | 日油株式会社 | 重合性ポリオキシアルキレンモノアルキルエーテル誘導体、該誘導体の重合体及び該重合体を含有する分散剤 |
| US6642422B2 (en) | 1998-06-17 | 2003-11-04 | Nof Corporation | Polyoxyalkylene monoalkyl ether, process for producing the same, polymerizable polyoxyalkylene monoalky ether derivative, polymer of said derivative and dispersant comprising said polymer |
| JP2001220440A (ja) * | 2000-02-10 | 2001-08-14 | Kao Corp | ポリアルキレングリコールエーテルの製造方法 |
| SE523934C2 (sv) * | 2001-09-24 | 2004-06-01 | Perstorp Specialty Chem Ab | Förfarande för av alkoxylering av di-, tri och polyalkoholer |
-
2003
- 2003-05-02 ES ES03728021T patent/ES2295586T3/es not_active Expired - Lifetime
- 2003-05-02 US US10/500,554 patent/US7402644B2/en not_active Expired - Lifetime
- 2003-05-02 DE DE60318431T patent/DE60318431T2/de not_active Expired - Lifetime
- 2003-05-02 JP JP2004506388A patent/JP5084102B2/ja not_active Expired - Fee Related
- 2003-05-02 WO PCT/JP2003/005602 patent/WO2003097716A1/en not_active Ceased
- 2003-05-02 EP EP03728021A patent/EP1507815B1/en not_active Revoked
-
2010
- 2010-03-05 JP JP2010049533A patent/JP5416618B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1507815A1 (en) | 2005-02-23 |
| US7402644B2 (en) | 2008-07-22 |
| US20050080298A1 (en) | 2005-04-14 |
| JP2010150556A (ja) | 2010-07-08 |
| EP1507815B1 (en) | 2008-01-02 |
| EP1507815A4 (en) | 2006-01-18 |
| JP5416618B2 (ja) | 2014-02-12 |
| DE60318431T2 (de) | 2009-01-02 |
| DE60318431D1 (de) | 2008-02-14 |
| JP5084102B2 (ja) | 2012-11-28 |
| WO2003097716A1 (en) | 2003-11-27 |
| JP2005526159A (ja) | 2005-09-02 |
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