JPS63251410A - ポリ−α−ヒドロキシアクリル酸に対応するポリラクトンの製造方法 - Google Patents
ポリ−α−ヒドロキシアクリル酸に対応するポリラクトンの製造方法Info
- Publication number
- JPS63251410A JPS63251410A JP62085837A JP8583787A JPS63251410A JP S63251410 A JPS63251410 A JP S63251410A JP 62085837 A JP62085837 A JP 62085837A JP 8583787 A JP8583787 A JP 8583787A JP S63251410 A JPS63251410 A JP S63251410A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- basic substance
- acid ester
- plac
- polymerization
- 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.)
- Granted
Links
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000002253 acid Substances 0.000 claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- -1 α,β-dichloropropionic acid ester Chemical class 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002685 polymerization catalyst Substances 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 5
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 27
- GKFWNPPZHDYVLI-UHFFFAOYSA-N 2,3-dichloropropanoic acid Chemical compound OC(=O)C(Cl)CCl GKFWNPPZHDYVLI-UHFFFAOYSA-N 0.000 abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 4
- OFHMODDLBXETIK-UHFFFAOYSA-N methyl 2,3-dichloropropanoate Chemical compound COC(=O)C(Cl)CCl OFHMODDLBXETIK-UHFFFAOYSA-N 0.000 abstract description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BNGQLYQWSYXQLK-UHFFFAOYSA-M sodium;2-chloroprop-2-enoate Chemical compound [Na+].[O-]C(=O)C(Cl)=C BNGQLYQWSYXQLK-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- KHOSEHYGRBUMBH-UHFFFAOYSA-N 2,3,3-trichloropropanoic acid Chemical compound OC(=O)C(Cl)C(Cl)Cl KHOSEHYGRBUMBH-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- 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 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical class ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000013590 bulk material Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
- C08F8/16—Lactonisation
-
- 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
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/04—Acids; Metal salts or ammonium salts thereof
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62085837A JPS63251410A (ja) | 1987-04-09 | 1987-04-09 | ポリ−α−ヒドロキシアクリル酸に対応するポリラクトンの製造方法 |
| CH2362/87A CH672132A5 (de) | 1987-04-09 | 1987-06-22 | |
| DE3722289A DE3722289C2 (de) | 1987-04-09 | 1987-07-06 | Verfahren zur Herstellung eines Polyactons einer Poly-Alpha-Hydroxyacrylsäure |
| KR1019870010502A KR910004486B1 (ko) | 1987-04-09 | 1987-09-22 | 폴리-α-히드록시 아크릴산에 상당하는 폴리락톤의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62085837A JPS63251410A (ja) | 1987-04-09 | 1987-04-09 | ポリ−α−ヒドロキシアクリル酸に対応するポリラクトンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63251410A true JPS63251410A (ja) | 1988-10-18 |
| JPH0571041B2 JPH0571041B2 (de) | 1993-10-06 |
Family
ID=13869972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62085837A Granted JPS63251410A (ja) | 1987-04-09 | 1987-04-09 | ポリ−α−ヒドロキシアクリル酸に対応するポリラクトンの製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS63251410A (de) |
| KR (1) | KR910004486B1 (de) |
| CH (1) | CH672132A5 (de) |
| DE (1) | DE3722289C2 (de) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0220517A (ja) * | 1988-07-04 | 1990-01-24 | Sandoz Ag | ポリー（α−ヒドロキシカルボキシレート）の製法 |
| US6120556A (en) * | 1996-06-21 | 2000-09-19 | Nippon Peroxide Co., Ltd. | Stabilizing agent for peroxide-bleaching procedure and methods of bleaching a fiber material by using same |
| JP2017165845A (ja) * | 2016-03-15 | 2017-09-21 | 株式会社日本触媒 | ラクトン環含有重合体の製造方法、重合体およびラクトン環含有重合体 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2061584A1 (en) * | 1970-12-15 | 1972-07-06 | Henkel & Cie Gmbh | Water insol alpha-substd-polyacrylates - obtd by basic treatment of alpha, beta-dichloro and/or dibromo propionic acids (est |
| DE2211256C2 (de) * | 1972-03-09 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Poly-α-oxy-acrylsäure |
| LU68037A1 (de) * | 1973-07-18 | 1975-04-11 | ||
| LU68060A1 (de) * | 1973-07-20 | 1975-04-11 | ||
| DE2346500C2 (de) * | 1973-09-15 | 1982-10-14 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Poly-α-oxyacrylsäure |
-
1987
- 1987-04-09 JP JP62085837A patent/JPS63251410A/ja active Granted
- 1987-06-22 CH CH2362/87A patent/CH672132A5/de not_active IP Right Cessation
- 1987-07-06 DE DE3722289A patent/DE3722289C2/de not_active Expired - Fee Related
- 1987-09-22 KR KR1019870010502A patent/KR910004486B1/ko not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0220517A (ja) * | 1988-07-04 | 1990-01-24 | Sandoz Ag | ポリー（α−ヒドロキシカルボキシレート）の製法 |
| US6120556A (en) * | 1996-06-21 | 2000-09-19 | Nippon Peroxide Co., Ltd. | Stabilizing agent for peroxide-bleaching procedure and methods of bleaching a fiber material by using same |
| JP2017165845A (ja) * | 2016-03-15 | 2017-09-21 | 株式会社日本触媒 | ラクトン環含有重合体の製造方法、重合体およびラクトン環含有重合体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0571041B2 (de) | 1993-10-06 |
| CH672132A5 (de) | 1989-10-31 |
| KR880012667A (ko) | 1988-11-28 |
| DE3722289C2 (de) | 1996-05-15 |
| KR910004486B1 (ko) | 1991-06-29 |
| DE3722289A1 (de) | 1988-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3517429B2 (ja) | 弗素化カルボン酸の精製方法 | |
| JPS604151A (ja) | テレフタル酸ジエステルの製造方法 | |
| CN110790851B (zh) | 一种水解聚马来酸酐的合成方法 | |
| JPS63251410A (ja) | ポリ−α−ヒドロキシアクリル酸に対応するポリラクトンの製造方法 | |
| JP4456939B2 (ja) | アダマンチルエステル類の精製方法 | |
| RO115426B1 (ro) | Procedeu de preparare a schimbatorilor anionici, slab bazici | |
| JP4279092B2 (ja) | アダマンチルエステル化合物の製造方法 | |
| JPS6355527B2 (de) | ||
| JPH0210137B2 (de) | ||
| JPH01503538A (ja) | テトラブロモフタル酸アルキルの製造方法 | |
| JP2686824B2 (ja) | ジペンタエリスリトールヘキサエステル化合物の製法 | |
| JP2003137837A (ja) | １，３，５−アダマンタントリオールモノ（メタ）アクリレートの製造法 | |
| JP3824403B2 (ja) | ３，５−ビス（トリフルオロメチル）ヨードベンゼンの製造方法 | |
| JPH04316566A (ja) | 脂環式オレフィンのエポキシ化物の製造方法 | |
| JPH044303B2 (de) | ||
| JPH0196177A (ja) | エポキシ化（メタ）アクリレート化合物の製造方法 | |
| JPH07206763A (ja) | 精製３，３’，４，４’−ビフェニルテトラカルボン酸又はその酸二無水物の製造方法 | |
| JP4303685B2 (ja) | ２−シクロペンテン−１−オンの製造方法 | |
| JPH01160969A (ja) | ２−置換イミダゾールの分離法 | |
| JP4570771B2 (ja) | ポリエステルからの２，６−ナフタレンジカルボン酸の回収 | |
| JPH0931018A (ja) | ペンタエリスリトール（メタ）アクリルエステル類の製造法 | |
| JP2903233B2 (ja) | 高純度のジフェニルジカルボン酸ジメチルの製造方法 | |
| JPH05320093A (ja) | ビフェニルジカルボン酸ジクロリドの製造方法 | |
| JPH0423642B2 (de) | ||
| JPS6312463B2 (de) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |