JPS5968327A - 不飽和ポリエステルの製造法 - Google Patents

不飽和ポリエステルの製造法

Info

Publication number: JPS5968327A
Authority: JP; Japan
Prior art keywords: reaction; acid; unsaturated; parts; polyalcohol
Prior art date: 1982-10-13
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

Application number

JP17961782A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0129209B2 (pl

Inventor

Shigeji Sato

佐藤　茂次

Hiroo Tadokoro

田所　博雄

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.)

Resonac Corp

Original Assignee

Hitachi Chemical 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.)

1982-10-13

Filing date

1982-10-13

Publication date

1984-04-18

1982-10-13 Application filed by Hitachi Chemical Co Ltd filed Critical Hitachi Chemical Co Ltd

1982-10-13 Priority to JP17961782A priority Critical patent/JPS5968327A/ja

1984-04-18 Publication of JPS5968327A publication Critical patent/JPS5968327A/ja

1989-06-08 Publication of JPH0129209B2 publication Critical patent/JPH0129209B2/ja

Status Granted legal-status Critical Current

Links

229920006305 unsaturated polyester Polymers 0.000 title claims abstract description 15
238000004519 manufacturing process Methods 0.000 title description 9
239000002253 acid Substances 0.000 claims abstract description 23
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims abstract description 19
150000005846 sugar alcohols Polymers 0.000 claims abstract description 14
238000005809 transesterification reaction Methods 0.000 claims abstract description 9
229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
239000003054 catalyst Substances 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 2
REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 32
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 26
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 15
239000002904 solvent Substances 0.000 abstract description 10
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract description 8
238000003860 storage Methods 0.000 abstract description 7
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract description 6
229940046892 lead acetate Drugs 0.000 abstract description 4
239000000203 mixture Substances 0.000 abstract description 4
229910021380 Manganese Chloride Inorganic materials 0.000 abstract description 3
GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 abstract description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 3
239000001530 fumaric acid Substances 0.000 abstract description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract description 3
239000011976 maleic acid Substances 0.000 abstract description 3
229940099607 manganese chloride Drugs 0.000 abstract description 3
235000002867 manganese chloride Nutrition 0.000 abstract description 3
239000011565 manganese chloride Substances 0.000 abstract description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 2
238000005886 esterification reaction Methods 0.000 abstract description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract description 2
239000008096 xylene Substances 0.000 abstract description 2
238000001816 cooling Methods 0.000 abstract 1
239000011541 reaction mixture Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229920005989 resin Polymers 0.000 description 11
239000011347 resin Substances 0.000 description 11
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 8
238000010438 heat treatment Methods 0.000 description 7
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Chemical group OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 7
229920000728 polyester Polymers 0.000 description 7
239000000126 substance Substances 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
229920006337 unsaturated polyester resin Polymers 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000007809 chemical reaction catalyst Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
-1 ethylene glycol Natural products 0.000 description 3
229920001225 polyester resin Polymers 0.000 description 3
239000004645 polyester resin Substances 0.000 description 3
238000001308 synthesis method Methods 0.000 description 3
229930185605 Bisphenol Natural products 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000007664 blowing Methods 0.000 description 2
229940120693 copper naphthenate Drugs 0.000 description 2
SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 2
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
JEKYMVBQWWZVHO-UHFFFAOYSA-N 1-chloro-2,2-dimethylpropane Chemical compound CC(C)(C)CCl JEKYMVBQWWZVHO-UHFFFAOYSA-N 0.000 description 1
ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 1
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
239000004135 Bone phosphate Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
235000017788 Cydonia oblonga Nutrition 0.000 description 1
239000004641 Diallyl-phthalate Substances 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000013040 bath agent Substances 0.000 description 1
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
229940018557 citraconic acid Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000001879 gelation Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1

Landscapes

Polyesters Or Polycarbonates (AREA)
Macromonomer-Based Addition Polymer (AREA)

JP17961782A 1982-10-13 1982-10-13 不飽和ポリエステルの製造法 Granted JPS5968327A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP17961782A JPS5968327A (ja)	1982-10-13	1982-10-13	不飽和ポリエステルの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP17961782A JPS5968327A (ja)	1982-10-13	1982-10-13	不飽和ポリエステルの製造法

Publications (2)

Publication Number	Publication Date
JPS5968327A true JPS5968327A (ja)	1984-04-18
JPH0129209B2 JPH0129209B2 (pl)	1989-06-08

Family

ID=16068880

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP17961782A Granted JPS5968327A (ja)	1982-10-13	1982-10-13	不飽和ポリエステルの製造法

Country Status (1)

Country	Link
JP (1)	JPS5968327A (pl)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5878295A (en) *	1995-05-10	1999-03-02	Olympus Optical Co., Ltd.	Shading device of a camera having collapsible bellows-like shading means

1982
- 1982-10-13 JP JP17961782A patent/JPS5968327A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5878295A (en) *	1995-05-10	1999-03-02	Olympus Optical Co., Ltd.	Shading device of a camera having collapsible bellows-like shading means

Also Published As

Publication number	Publication date
JPH0129209B2 (pl)	1989-06-08

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US4902773A (en)	1990-02-20	Method of preparation of unsaturated polyester resins from maleic acid/anhydride
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KR0182367B1 (ko)	1999-05-15	폴리에스테르 중합체의 제조방법
JP2001106882A (ja)	2001-04-17	液晶性ポリエステル樹脂組成物及びそれを用いた成形体
JP2574346B2 (ja)	1997-01-22	耐熱性不飽和化合物
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JPH09291140A (ja)	1997-11-11	高融点不飽和ポリエステルの製造方法
JPS58160314A (ja)	1983-09-22	ポリエステルの製造方法
JPS5922728B2 (ja)	1984-05-29	透明性の良いポリエステルの製造法
JPS62250027A (ja)	1987-10-30	ポリエチレンナフタレ−トの製造方法
JPS5947691B2 (ja)	1984-11-21	不飽和ポリエステルの製造方法
JPS6057445B2 (ja)	1985-12-14	ポリエステルの製造方法
JPS58118824A (ja)	1983-07-15	ポリエステルの製造方法
JPS59157116A (ja)	1984-09-06	ポリエステルの製造方法

JPS5968327A - 不飽和ポリエステルの製造法 - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=16068880

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Also Published As

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