CS212326B2 - Method of preparation of the copoly(carbonate/phosphonates - Google Patents

Method of preparation of the copoly(carbonate/phosphonates Download PDF

Info

Publication number: CS212326B2
Authority: CS; Czechoslovakia
Prior art keywords: added; carbonate; bisphenol; methylene chloride; reaction
Prior art date: 1978-08-11

Application number

CS795339A

Other languages

Czech (cs)

English (en)

Inventor

Siegfried Altscher

Kisco Kim

Arthur Jun-Shen Yu

Original Assignee

Stauffer Chemical Co

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.)

1978-08-11

Filing date

1979-08-02

Publication date

1982-03-26

1979-08-02 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1982-03-26 Publication of CS212326B2 publication Critical patent/CS212326B2/cs

Links

238000002360 preparation method Methods 0.000 title claims description 9
238000000034 method Methods 0.000 title claims description 6
229920001577 copolymer Chemical compound 0.000 title abstract description 23
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 30
239000006085 branching agent Substances 0.000 claims abstract description 19
238000006243 chemical reaction Methods 0.000 claims abstract description 19
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 15
239000003795 chemical substances by application Substances 0.000 claims abstract description 15
239000002243 precursor Substances 0.000 claims abstract description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 28
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 5
229940079877 pyrogallol Drugs 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
-1 phosphonates sulfates Chemical class 0.000 claims description 2
150000003018 phosphorus compounds Chemical class 0.000 claims description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 1
238000002844 melting Methods 0.000 abstract description 13
230000008018 melting Effects 0.000 abstract description 13
229920000642 polymer Polymers 0.000 abstract description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 92
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 58
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
239000000047 product Substances 0.000 description 29
239000000203 mixture Substances 0.000 description 25
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 19
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 14
KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 13
229960003742 phenol Drugs 0.000 description 13
229930185605 Bisphenol Natural products 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
238000002474 experimental method Methods 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 5
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
238000001879 gelation Methods 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 4
QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical compound OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 3
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 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
229920005668 polycarbonate resin Polymers 0.000 description 3
239000004431 polycarbonate resin Substances 0.000 description 3
XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
GFGBKRVRCSBZMV-UHFFFAOYSA-N ClOCl.[P]C1=CC=CC=C1 Chemical compound ClOCl.[P]C1=CC=CC=C1 GFGBKRVRCSBZMV-UHFFFAOYSA-N 0.000 description 2
101100520660 Drosophila melanogaster Poc1 gene Proteins 0.000 description 2
101100520662 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PBA1 gene Proteins 0.000 description 2
235000015107 ale Nutrition 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000005452 bending Methods 0.000 description 2
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
150000005205 dihydroxybenzenes Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000009477 glass transition Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
239000000178 monomer Substances 0.000 description 2
239000002516 radical scavenger Substances 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
AYNPIRVEWMUJDE-UHFFFAOYSA-N 2,5-dichlorohydroquinone Chemical compound OC1=CC(Cl)=C(O)C=C1Cl AYNPIRVEWMUJDE-UHFFFAOYSA-N 0.000 description 1
ZKZKMLKTQUCSNX-UHFFFAOYSA-N 2,6-dibromo-4-(3,5-dibromo-4-hydroxyphenyl)sulfinylphenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1S(=O)C1=CC(Br)=C(O)C(Br)=C1 ZKZKMLKTQUCSNX-UHFFFAOYSA-N 0.000 description 1
TXYQFJWVHVYIHB-UHFFFAOYSA-N 2,6-dichloro-4-(3,5-dichloro-4-hydroxyphenoxy)phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1OC1=CC(Cl)=C(O)C(Cl)=C1 TXYQFJWVHVYIHB-UHFFFAOYSA-N 0.000 description 1
HNDVYGDZLSXOAX-UHFFFAOYSA-N 2,6-dichloro-4-propylphenol Chemical compound CCCC1=CC(Cl)=C(O)C(Cl)=C1 HNDVYGDZLSXOAX-UHFFFAOYSA-N 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-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
YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
SUCTVKDVODFXFX-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)sulfonyl-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(S(=O)(=O)C=2C=C(C)C(O)=C(C)C=2)=C1 SUCTVKDVODFXFX-UHFFFAOYSA-N 0.000 description 1
NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 1
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
KNDDEFBFJLKPFE-UHFFFAOYSA-N 4-n-Heptylphenol Chemical compound CCCCCCCC1=CC=C(O)C=C1 KNDDEFBFJLKPFE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XMGGCBJKTROPMA-UHFFFAOYSA-N ClP(Cl)(=O)[ClH]C1=CC=CC=C1 Chemical compound ClP(Cl)(=O)[ClH]C1=CC=CC=C1 XMGGCBJKTROPMA-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 1
230000009194 climbing Effects 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000001788 irregular Effects 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000008379 phenol ethers Chemical class 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
150000003739 xylenols Chemical class 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

CS795339A 1978-08-11 1979-08-02 Method of preparation of the copoly(carbonate/phosphonates CS212326B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/932,840 US4223104A (en)	1978-08-11	1978-08-11	Copoly (carbonate/phosphonate) compositions

Publications (1)

Publication Number	Publication Date
CS212326B2 true CS212326B2 (en)	1982-03-26

Family

ID=25463033

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS795339A CS212326B2 (en)	1978-08-11	1979-08-02	Method of preparation of the copoly(carbonate/phosphonates

Country Status (11)

Country	Link
US (1)	US4223104A (de)
EP (1)	EP0008823B1 (de)
JP (1)	JPS5525476A (de)
AU (1)	AU525229B2 (de)
CA (1)	CA1121096A (de)
CS (1)	CS212326B2 (de)
DD (1)	DD145756A5 (de)
DE (1)	DE2963490D1 (de)
IL (1)	IL57545A (de)
MA (1)	MA18529A1 (de)
NO (1)	NO792604L (de)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2925208A1 (de) *	1979-06-22	1981-01-29	Bayer Ag	Verfahren zur herstellung von aromatischen thermoplastischen polyphosphonatocarbonaten
DE2925207A1 (de) *	1979-06-22	1981-01-29	Bayer Ag	Thermoplastische, verzweigte, aromatische polyphosphonate, ihre verwendung und ein verfahren zu ihrer herstellung
DE3001863A1 (de) *	1980-01-19	1981-07-23	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von thermoplastischen aromatischen polyphosphonatocarbonaten verbesserter thermischer alterungsbestaendigkeit und deren verwendung
US4444978A (en) *	1983-07-29	1984-04-24	The Dow Chemical Company	Thermally stable carbonate polymer
US4474937A (en) *	1983-10-03	1984-10-02	The Dow Chemical Company	Phosphorus-modified polyestercarbonate resins
DE3517271A1 (de) *	1985-05-14	1986-11-20	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von copolyphosphonaten mit hoher kerbschlagzaehigkeit
DE3520296A1 (de) *	1985-06-07	1986-12-11	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von copolyphosphonaten mit hoher zaehigkeit
DE3933548A1 (de) *	1989-10-07	1991-04-11	Bayer Ag	Hochverzweigte polyphosphonate
US20040167283A1 (en) *	2003-02-24	2004-08-26	Michael Vinciguerra	Linear polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto
US6861499B2 (en) *	2003-02-24	2005-03-01	Triton Systems, Inc.	Branched polyphosphonates that exhibit an advantageous combination of properties, and methods related thereto
US7645850B2 (en) *	2005-08-11	2010-01-12	Frx Polymers, Inc.	Poly(block-phosphonato-ester) and poly(block-phosphonato-carbonate) and methods of making same
US7666932B2 (en) *	2005-10-17	2010-02-23	Frx Polymers, Inc.	Compositions comprising polyphosphonates and additives that exhibit an advantageous combination of properties, and methods related thereto
WO2007079272A2 (en) *	2005-10-18	2007-07-12	Frx Polymers Llc	Diaryl alkylphosphonates and methods for preparing same
US7838604B2 (en) *	2005-12-01	2010-11-23	Frx Polymers, Inc.	Method for the production of block copolycarbonate/phosphonates and compositions therefrom
US7928259B2 (en) *	2008-02-12	2011-04-19	Frx Polymers, Inc.	Diaryl alkylphosphonates and methods for preparing same
US9441877B2 (en)	2010-03-17	2016-09-13	Chart Inc.	Integrated pre-cooled mixed refrigerant system and method
EP2616496A4 (de)	2010-09-16	2016-05-18	Frx Polymers Inc	Zufällige bisphenol-copoly(phosphonat-carbonate) mit hohem molekulargewicht
KR20140086774A (ko) *	2012-12-28	2014-07-08	제일모직주식회사	분지형 폴리카보네이트 및 이의 제조방법
JP2016510355A (ja)	2013-01-22	2016-04-07	エフアールエックスポリマーズ、インク．	リン含有エポキシ化合物およびそれからなる組成物
US11428463B2 (en)	2013-03-15	2022-08-30	Chart Energy & Chemicals, Inc.	Mixed refrigerant system and method
CN108955084B (zh)	2013-03-15	2020-10-30	查特能源化工公司	混合制冷剂***和方法
US11408673B2 (en)	2013-03-15	2022-08-09	Chart Energy & Chemicals, Inc.	Mixed refrigerant system and method
AR105277A1 (es)	2015-07-08	2017-09-20	Chart Energy & Chemicals Inc	Sistema y método de refrigeración mixta

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3094508A (en) *	1959-04-16	1963-06-18	Armstrong Cork Co	Branched polycarbonate and process for preparing same
GB1025422A (en) *	1961-11-30	1966-04-06	Gevaert Photo Prod Nv	Copolyesters and the preparation thereof
BE754758A (fr) *	1969-08-19	1971-01-18	Gen Electric	Composition thermiquement stable a base de polymere de carbonate aromatique et procede pour sa preparation
US3597394A (en) *	1969-10-16	1971-08-03	Mobay Chemical Corp	Branching or crosslinking of polycarbonates
US4001183A (en) *	1971-03-19	1977-01-04	Bayer Aktiengesellschaft	Tetraphenol containing polycarbonates
US3766139A (en) *	1971-07-29	1973-10-16	Gen Electric	Thermal oxidatively stable polycarbonate composition
DE2254918A1 (de) *	1972-11-09	1974-05-16	Bayer Ag	Verzweigte aromatische polycarbonate

1978
- 1978-08-11 US US05/932,840 patent/US4223104A/en not_active Expired - Lifetime
1979
- 1979-06-12 IL IL57545A patent/IL57545A/xx unknown
- 1979-06-15 AU AU48134/79A patent/AU525229B2/en not_active Ceased
- 1979-06-22 CA CA000330353A patent/CA1121096A/en not_active Expired
- 1979-07-06 JP JP8581279A patent/JPS5525476A/ja active Pending
- 1979-07-16 MA MA18726A patent/MA18529A1/fr unknown
- 1979-08-02 CS CS795339A patent/CS212326B2/cs unknown
- 1979-08-08 DE DE7979200438T patent/DE2963490D1/de not_active Expired
- 1979-08-08 EP EP79200438A patent/EP0008823B1/de not_active Expired
- 1979-08-09 DD DD79214894A patent/DD145756A5/de unknown
- 1979-08-10 NO NO792604A patent/NO792604L/no unknown

Also Published As

Publication number	Publication date
JPS5525476A (en)	1980-02-23
AU4813479A (en)	1980-02-14
DD145756A5 (de)	1981-01-07
US4223104A (en)	1980-09-16
DE2963490D1 (en)	1982-09-30
CA1121096A (en)	1982-03-30
EP0008823A1 (de)	1980-03-19
MA18529A1 (fr)	1980-04-01
NO792604L (no)	1980-02-12
EP0008823B1 (de)	1982-08-04
AU525229B2 (en)	1982-10-28
IL57545A (en)	1983-07-31
IL57545A0 (en)	1979-10-31

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