JPH0571041B2 - - Google Patents

Info

Publication number: JPH0571041B2
Authority: JP; Japan
Prior art keywords: acid; plac; polymerization; basic substance; chloroacrylate
Prior art date: 1987-04-09
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 - Fee Related

Application number

JP62085837A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63251410A (ja

Inventor

Ryuichi Kayama

Hiroyuki Suzuki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Peroxide Co Ltd

Original Assignee

Nippon Peroxide Co Ltd

Priority date (The priority date 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 date listed.)

1987-04-09

Filing date

1987-04-09

Publication date

1993-10-06

1987-04-09 Application filed by Nippon Peroxide Co Ltd filed Critical Nippon Peroxide Co Ltd

1987-04-09 Priority to JP62085837A priority Critical patent/JPS63251410A/ja

1987-06-22 Priority to CH2362/87A priority patent/CH672132A5/de

1987-07-06 Priority to DE3722289A priority patent/DE3722289C2/de

1987-09-22 Priority to KR1019870010502A priority patent/KR910004486B1/ko

1988-10-18 Publication of JPS63251410A publication Critical patent/JPS63251410A/ja

1993-10-06 Publication of JPH0571041B2 publication Critical patent/JPH0571041B2/ja

Status Granted legal-status Critical Current

Links

238000000034 method Methods 0.000 claims description 45
239000000126 substance Substances 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
238000006116 polymerization reaction Methods 0.000 claims description 19
-1 α,β-dichloropropionic acid ester Chemical class 0.000 claims description 19
239000007864 aqueous solution Substances 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 10
238000010438 heat treatment Methods 0.000 claims description 10
239000002685 polymerization catalyst Substances 0.000 claims description 8
239000006227 byproduct Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 claims description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 7
GKFWNPPZHDYVLI-UHFFFAOYSA-N 2,3-dichloropropanoic acid Chemical compound OC(=O)C(Cl)CCl GKFWNPPZHDYVLI-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
235000017281 sodium acetate Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
239000002994 raw material Substances 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000007033 dehydrochlorination reaction Methods 0.000 description 4
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
OFHMODDLBXETIK-UHFFFAOYSA-N methyl 2,3-dichloropropanoate Chemical compound COC(=O)C(Cl)CCl OFHMODDLBXETIK-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000002699 waste material Substances 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
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
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 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation 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
230000000379 polymerizing effect Effects 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 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
ZMYAKSMZTVWUJB-UHFFFAOYSA-N 2,3-dibromopropanoic acid Chemical compound OC(=O)C(Br)CBr ZMYAKSMZTVWUJB-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
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-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
235000011054 acetic acid Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940048053 acrylate Drugs 0.000 description 1
125000005396 acrylic acid ester group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical class 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
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
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003599 detergent Substances 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
238000005516 engineering process Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 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
239000003999 initiator Substances 0.000 description 1
239000013067 intermediate product Substances 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 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
229920000728 polyester Polymers 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
229940047670 sodium acrylate 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
BNGQLYQWSYXQLK-UHFFFAOYSA-M sodium;2-chloroprop-2-enoate Chemical compound [Na+].[O-]C(=O)C(Cl)=C BNGQLYQWSYXQLK-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
238000001228 spectrum Methods 0.000 description 1
238000003786 synthesis reaction Methods 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)

JP62085837A 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 Granted JPS63251410A (ja)

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 JPS63251410A (ja)	1988-10-18
JPH0571041B2 true 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)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2798212B2 (ja) *	1988-07-04	1998-09-17	クラリアントファイナンス（ビーブイアイ）リミティド	ポリー（α−ヒドロキシカルボキシレート）の製法
JPH108092A (ja) *	1996-06-21	1998-01-13	Mitsubishi Paper Mills Ltd	過酸化物漂白用安定化剤及びそれを用いた繊維系物質の漂白方法
JP6734081B2 (ja) *	2016-03-15	2020-08-05	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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number	Publication date
KR910004486B1 (ko)	1991-06-29
JPS63251410A (ja)	1988-10-18
KR880012667A (ko)	1988-11-28
CH672132A5 (de)	1989-10-31
DE3722289C2 (de)	1996-05-15
DE3722289A1 (de)	1988-10-27

Legal Events

Date	Code	Title	Description
2006-10-06	LAPS	Cancellation because of no payment of annual fees

Publication	Publication Date	Title
JPH03118355A (ja)	1991-05-20	１―アミノメチル―１―シクロヘキサン酢酸の調製方法
JP3066859B2 (ja)	2000-07-17	塩含量の低いビニルアミンポリマーの一段階製造
JPH0571041B2 (de)	1993-10-06
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JP4279092B2 (ja)	2009-06-17	アダマンチルエステル化合物の製造方法
JPH0210137B2 (de)	1990-03-06
JP2870183B2 (ja)	1999-03-10	１，３―フェニレンジオキシジ酢酸の製法
JPH01503538A (ja)	1989-11-30	テトラブロモフタル酸アルキルの製造方法
JP2686824B2 (ja)	1997-12-08	ジペンタエリスリトールヘキサエステル化合物の製法
JP3222941B2 (ja)	2001-10-29	カルボン酸の製造法
KR970005475B1 (ko)	1997-04-16	폴리-[α-히드록시-(아크릴,크로톤,또는 아크릴+크로톤)산]의 폴리락톤류 및 상응하는 염류의 제조방법
JPH0423642B2 (de)	1992-04-22
JP2971523B2 (ja)	1999-11-08	トリアリルイソシアヌレートの製造法
JP4184714B2 (ja)	2008-11-19	重水素化メタクリル酸メチルの製造方法
JPH045657B2 (de)	1992-02-03
JP3831021B2 (ja)	2006-10-11	２−インダノン類の製造方法
US4107411A (en)	1978-08-15	Method of preparing salts of poly-alpha-hydroxyacrylic acid
JPH0672124B2 (ja)	1994-09-14	４−クロロフタル酸の製法
JP4246447B2 (ja)	2009-04-02	重水素化メタクリル酸メチルの製造方法
JPH01258643A (ja)	1989-10-16	多官能（メタ）アクリル酸エステルの製造法
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