PL149676B1 - Method for manufacturing polyestrols containing chemically bounded bromium - Google Patents

Method for manufacturing polyestrols containing chemically bounded bromium

Info

Publication number: PL149676B1
Authority: PL; Poland
Prior art keywords: glycol; bromine; general formula; polyester; h0ch
Prior art date: 1987-03-09

Application number

PL1987264530A

Other languages

English (en)

Polish (pl)

Other versions

PL264530A1 (en

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

1987-03-09

Publication date

1990-03-31

1987-03-09 Application filed filed Critical

1987-03-09 Priority to PL1987264530A priority Critical patent/PL149676B1/pl

1988-03-07 Priority to DD88313477A priority patent/DD275249A5/de

1988-03-08 Priority to IT8819690A priority patent/IT1216022B/it

1988-03-08 Priority to DE3807581A priority patent/DE3807581A1/de

1988-03-09 Priority to JP63053886A priority patent/JPH01221422A/ja

1988-10-13 Publication of PL264530A1 publication Critical patent/PL264530A1/xx

1990-03-31 Publication of PL149676B1 publication Critical patent/PL149676B1/pl

Links

229910052794 bromium Inorganic materials 0.000 title claims description 36
238000000034 method Methods 0.000 title claims description 14
238000004519 manufacturing process Methods 0.000 title claims description 7
150000001648 bromium Chemical class 0.000 title 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 36
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 35
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
229920000728 polyester Polymers 0.000 claims description 33
150000002334 glycols Chemical class 0.000 claims description 16
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 15
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 10
229920006395 saturated elastomer Polymers 0.000 claims description 9
238000004821 distillation Methods 0.000 claims description 6
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
229920006305 unsaturated polyester Polymers 0.000 claims description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
230000031709 bromination Effects 0.000 claims description 4
238000005893 bromination reaction Methods 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
150000008064 anhydrides Chemical class 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
238000010438 heat treatment Methods 0.000 claims 4
-1 aromatic dicarboxylic acids Chemical class 0.000 claims 3
238000000926 separation method Methods 0.000 claims 2
239000001384 succinic acid Substances 0.000 claims 2
239000004721 Polyphenylene oxide Substances 0.000 claims 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims 1
229920000570 polyether Polymers 0.000 claims 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 7
229910000042 hydrogen bromide Inorganic materials 0.000 description 6
238000006068 polycondensation reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
125000003158 alcohol group Chemical group 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
125000003827 glycol group Chemical group 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical group OCCOCCOCCO ZIBGPFATKBEMQZ-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
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
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
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical class C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 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
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010348 incorporation Methods 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
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical group OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000000203 mixture Substances 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
229920005906 polyester polyol Polymers 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 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)

PL1987264530A 1987-03-09 1987-03-09 Method for manufacturing polyestrols containing chemically bounded bromium PL149676B1 (en)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
PL1987264530A PL149676B1 (en)	1987-03-09	1987-03-09	Method for manufacturing polyestrols containing chemically bounded bromium
DD88313477A DD275249A5 (de)	1987-03-09	1988-03-07	Verfahren zur herstellung von polyestrolen, welche chemisch gebundenes brom enthalten
IT8819690A IT1216022B (it)	1987-03-09	1988-03-08	Procedimento per la produzione di poliesteri polioli che contengono bromo chimicamente legato.
DE3807581A DE3807581A1 (de)	1987-03-09	1988-03-08	Verfahren zur herstellung von polyestrolen, die chemisch gebundenes brom enthalten
JP63053886A JPH01221422A (ja)	1987-03-09	1988-03-09	臭素化ポリエステルポリオールの製造方法

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 (2)

Publication Number	Publication Date
PL264530A1 PL264530A1 (en)	1988-10-13
PL149676B1 true PL149676B1 (en)	1990-03-31

Family

ID=20035343

Family Applications (1)

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

Country Status (5)

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

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
DD275249A5 (de)	1990-01-17
IT8819690A0 (it)	1988-03-08
JPH01221422A (ja)	1989-09-04
PL264530A1 (en)	1988-10-13
DE3807581A1 (de)	1988-09-22
IT1216022B (it)	1990-02-22

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PL149676B1 (en)	1990-03-31	Method for manufacturing polyestrols containing chemically bounded bromium
JP3153875B2 (ja)	2001-04-09	難燃性のポリエステルポリオール組成物
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US4716213A (en)	1987-12-29	Polyesters polyols prepared from glutaric acid, succinic acid and adipic acid, and polyurethanes prepared therefrom
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PL151999B1 (pl)	1990-10-31	Sposób wytwarzania poliestroli
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