DD275249A5 - Verfahren zur herstellung von polyestrolen, welche chemisch gebundenes brom enthalten - Google Patents

Verfahren zur herstellung von polyestrolen, welche chemisch gebundenes brom enthalten Download PDF

Info

Publication number: DD275249A5
Authority: DD; German Democratic Republic
Prior art keywords: glycol; polyestrol; bromine; general formula; added
Prior art date: 1987-03-09

Application number

DD88313477A

Other languages

German (de)

English (en)

Inventor

Piotr Penczek

Ryszard Ostrysz

Stefan Janiszewski

Original Assignee

��@��@��k��

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.)

1987-03-09

Filing date

1988-03-07

Publication date

1990-01-17

1988-03-07 Application filed by ��@��@��k�� filed Critical ��@��@��k��

1990-01-17 Publication of DD275249A5 publication Critical patent/DD275249A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
125000001246 bromo group Chemical class Br* 0.000 title 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 47
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 38
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 38
229910052794 bromium Inorganic materials 0.000 claims abstract description 38
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 19
238000000034 method Methods 0.000 claims abstract description 19
230000031709 bromination Effects 0.000 claims abstract description 8
238000005893 bromination reaction Methods 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 7
150000002334 glycols Chemical class 0.000 claims description 18
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 12
150000005846 sugar alcohols Polymers 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 10
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 8
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
230000008030 elimination Effects 0.000 claims description 6
238000003379 elimination reaction Methods 0.000 claims description 6
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 5
238000004821 distillation Methods 0.000 claims description 5
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
239000001361 adipic acid Substances 0.000 claims description 4
235000011037 adipic acid Nutrition 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
150000004702 methyl esters Chemical class 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
-1 aromatic dicarboxylic acids Chemical class 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
230000008034 disappearance Effects 0.000 claims description 2
235000011187 glycerol Nutrition 0.000 claims description 2
230000034659 glycolysis Effects 0.000 claims description 2
239000001384 succinic acid Substances 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
238000010438 heat treatment Methods 0.000 claims 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract description 20
229910000042 hydrogen bromide Inorganic materials 0.000 abstract description 10
229920005862 polyol Polymers 0.000 abstract description 9
150000003077 polyols Chemical class 0.000 abstract description 9
239000004814 polyurethane Substances 0.000 abstract description 4
229920002635 polyurethane Polymers 0.000 abstract description 4
238000005260 corrosion Methods 0.000 abstract description 3
230000007797 corrosion Effects 0.000 abstract description 3
239000012535 impurity Substances 0.000 abstract description 3
239000002184 metal Substances 0.000 abstract description 3
229910052751 metal Inorganic materials 0.000 abstract description 3
238000007086 side reaction Methods 0.000 abstract description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 abstract 1
101150065749 Churc1 gene Proteins 0.000 abstract 1
102100038239 Protein Churchill Human genes 0.000 abstract 1
239000002253 acid Substances 0.000 description 9
238000006068 polycondensation reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000003158 alcohol group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
238000005809 transesterification reaction Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
239000011244 liquid electrolyte Substances 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
150000005217 methyl ethers Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000005829 trimerization reaction Methods 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
- C08G63/91—Polymers modified by chemical after-treatment
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4607—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen having halogens
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- 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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation

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)
Polyesters Or Polycarbonates (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyethers (AREA)

DD88313477A 1987-03-09 1988-03-07 Verfahren zur herstellung von polyestrolen, welche chemisch gebundenes brom enthalten DD275249A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PL1987264530A PL149676B1 (en)	1987-03-09	1987-03-09	Method for manufacturing polyestrols containing chemically bounded bromium

Publications (1)

Publication Number	Publication Date
DD275249A5 true DD275249A5 (de)	1990-01-17

Family

ID=20035343

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88313477A DD275249A5 (de)	1987-03-09	1988-03-07	Verfahren zur herstellung von polyestrolen, welche chemisch gebundenes brom enthalten

Country Status (5)

Country	Link
JP (1)	JPH01221422A (pl)
DD (1)	DD275249A5 (pl)
DE (1)	DE3807581A1 (pl)
IT (1)	IT1216022B (pl)
PL (1)	PL149676B1 (pl)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1263297B (de) *	1960-10-27	1968-03-14	Huels Chemische Werke Ag	Herstellen flammwidriger Polyester-Formteile

1987
- 1987-03-09 PL PL1987264530A patent/PL149676B1/pl unknown
1988
- 1988-03-07 DD DD88313477A patent/DD275249A5/de not_active IP Right Cessation
- 1988-03-08 DE DE3807581A patent/DE3807581A1/de not_active Ceased
- 1988-03-08 IT IT8819690A patent/IT1216022B/it active
- 1988-03-09 JP JP63053886A patent/JPH01221422A/ja active Pending

Also Published As

Publication number	Publication date
DE3807581A1 (de)	1988-09-22
PL149676B1 (en)	1990-03-31
JPH01221422A (ja)	1989-09-04
IT8819690A0 (it)	1988-03-08
PL264530A1 (en)	1988-10-13
IT1216022B (it)	1990-02-22

Legal Events

Date	Code	Title	Description
1999-12-09	ENJ	Ceased due to non-payment of renewal fee

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