CA1088238A - Flame-retardant polyphenylene ether resin composition - Google Patents

Flame-retardant polyphenylene ether resin composition

Info

Publication number: CA1088238A
Authority: CA; Canada
Prior art keywords: group; resin composition; composition according; organic phosphorus; yxy
Prior art date: 1976-07-05
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

Application number

CA282,053A

Other languages

English (en)

French (fr)

Inventor

Shinichi Izawa

Jun Sugiyama

Tsutomu Tanaka

Atsuo Nakanishi

Toranosuke Saito

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.)

Sanko Kaihatsu Kagaku Kenkyusho KK

Asahi Dow Ltd

Original Assignee

Sanko Kaihatsu Kagaku Kenkyusho KK

Asahi Dow 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.)

1976-07-05

Filing date

1977-07-05

Publication date

1980-10-21

1977-07-05 Application filed by Sanko Kaihatsu Kagaku Kenkyusho KK, Asahi Dow Ltd filed Critical Sanko Kaihatsu Kagaku Kenkyusho KK

1980-10-21 Application granted granted Critical

1980-10-21 Publication of CA1088238A publication Critical patent/CA1088238A/en

Status Expired legal-status Critical Current

Links

229920001955 polyphenylene ether Polymers 0.000 title claims abstract description 29
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 title claims abstract description 7
239000003063 flame retardant Substances 0.000 title claims abstract description 7
239000011342 resin composition Substances 0.000 title claims description 71
150000002903 organophosphorus compounds Chemical class 0.000 claims abstract description 59
150000001875 compounds Chemical class 0.000 claims abstract description 25
239000000203 mixture Substances 0.000 claims abstract description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
229920005989 resin Polymers 0.000 claims abstract description 22
239000011347 resin Substances 0.000 claims abstract description 22
-1 aromatic amino compound Chemical class 0.000 claims abstract description 19
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
125000005843 halogen group Chemical group 0.000 claims abstract description 5
229920000642 polymer Polymers 0.000 claims description 22
229920000578 graft copolymer Polymers 0.000 claims description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 9
229920002554 vinyl polymer Polymers 0.000 claims description 6
238000006116 polymerization reaction Methods 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
229910052801 chlorine Inorganic materials 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
239000004793 Polystyrene Substances 0.000 abstract description 10
229920002223 polystyrene Polymers 0.000 abstract description 10
125000003277 amino group Chemical group 0.000 abstract description 4
239000002994 raw material Substances 0.000 abstract 1
238000007493 shaping process Methods 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
238000000034 method Methods 0.000 description 36
238000012360 testing method Methods 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000000047 product Substances 0.000 description 18
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
229920002857 polybutadiene Polymers 0.000 description 11
239000005062 Polybutadiene Substances 0.000 description 9
239000008188 pellet Substances 0.000 description 9
229910052698 phosphorus Inorganic materials 0.000 description 9
235000014786 phosphorus Nutrition 0.000 description 9
239000011574 phosphorus Substances 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000011369 resultant mixture Substances 0.000 description 6
238000000862 absorption spectrum Methods 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
238000002156 mixing Methods 0.000 description 3
FOZNBFJYVWWMSZ-UHFFFAOYSA-N 1-N,4-N-bis(methoxymethyl)benzene-1,4-diamine Chemical compound COCNC1=CC=C(C=C1)NCOC FOZNBFJYVWWMSZ-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000007547 defect Effects 0.000 description 2
230000002950 deficient Effects 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000010559 graft polymerization reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
150000003018 phosphorus compounds Chemical class 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
229920001890 Novodur Polymers 0.000 description 1
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229920006026 co-polymeric resin Polymers 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000004898 kneading Methods 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
238000000465 moulding Methods 0.000 description 1
238000005453 pelletization Methods 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000005060 rubber Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA282,053A 1976-07-05 1977-07-05 Flame-retardant polyphenylene ether resin composition Expired CA1088238A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP78893/76		1976-07-05
JP51078893A JPS5925822B2 (ja)	1976-07-05	1976-07-05	難燃性ポリフエニレンエ−テル樹脂組成物

Publications (1)

Publication Number	Publication Date
CA1088238A true CA1088238A (en)	1980-10-21

Family

ID=13674482

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA282,053A Expired CA1088238A (en)	1976-07-05	1977-07-05	Flame-retardant polyphenylene ether resin composition

Country Status (6)

Country	Link
JP (1)	JPS5925822B2 (de)
CA (1)	CA1088238A (de)
DE (1)	DE2730345C3 (de)
FR (1)	FR2357602A1 (de)
GB (1)	GB1567849A (de)
NL (1)	NL166271C (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0269011A (ja) *	1988-09-05	1990-03-08	Takayuki Chikaki	音質調整装置
CH699311B1 (de)	2008-08-14	2012-03-30	Ems Patent Ag	Verfahren zur Herstellung von Dibenz[c,e][1,2]-oxaphosphorin-Derivaten, Amino-dibenz[c,e][1,2]-oxaphosphorin sowie deren Verwendung.
CH699310B1 (de)	2008-08-14	2012-03-30	Ems Patent Ag	Verfahren zur Herstellung von verbrückten Dibenz[c,e][1,2]-oxaphosphorin-6-oxiden.
EP3540000A1 (de)	2018-03-16	2019-09-18	Stutz, Felix Benjamin	Flammhemmendes polyamid 6-masterbatch und daraus hergestellte fasern
WO2023153508A1 (ja) *	2022-02-14	2023-08-17	三光株式会社	高屈折率を示す、トリアジン環を有する新規なジヒドロオキサフォスファフェナントレン誘導体及びその製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1555489A (en) *	1975-06-16	1979-11-14	Ici Ltd	Process for preparing a granular herbicidal composition

1976
- 1976-07-05 JP JP51078893A patent/JPS5925822B2/ja not_active Expired
1977
- 1977-07-05 DE DE2730345A patent/DE2730345C3/de not_active Expired
- 1977-07-05 NL NL7707437.A patent/NL166271C/xx not_active IP Right Cessation
- 1977-07-05 GB GB28102/77A patent/GB1567849A/en not_active Expired
- 1977-07-05 CA CA282,053A patent/CA1088238A/en not_active Expired
- 1977-07-05 FR FR7720623A patent/FR2357602A1/fr active Granted

Also Published As

Publication number	Publication date
NL166271B (nl)	1981-02-16
DE2730345B2 (de)	1979-05-17
NL166271C (nl)	1981-07-15
GB1567849A (en)	1980-05-21
JPS535253A (en)	1978-01-18
DE2730345A1 (de)	1978-01-12
JPS5925822B2 (ja)	1984-06-21
FR2357602B1 (de)	1980-01-18
FR2357602A1 (fr)	1978-02-03
DE2730345C3 (de)	1980-01-10
NL7707437A (nl)	1978-01-09

Publication	Publication Date	Title
US4113795A (en)	1978-09-12	Flame-retardant polyphenylene ether resin composition
US4198492A (en)	1980-04-15	Flame-retardant polyphenylene ether resin composition
EP1070744A2 (de)	2001-01-24	Halogenfreie flammhemmende thermoplastische Formmassen
KR20120111502A (ko)	2012-10-10	열가소성 난연 ａｂｓ수지 조성물
US3887646A (en)	1975-06-03	Resinous compositions containing polyphenylene ether, styrene rubber and rubber-modified chlorostyrene polymer
CA1088238A (en)	1980-10-21	Flame-retardant polyphenylene ether resin composition
US20070259999A1 (en)	2007-11-08	Strenic thermoplastic resin composition
JPS5916576B2 (ja)	1984-04-16	難燃性ポリフエニレンエ−テル組成物
EP2770023B1 (de)	2016-08-31	Halogenfreie flammengehemmte Styrolharzzusammensetzung
CA1089579A (en)	1980-11-11	Flame-retardant polyphenylene ether resin composition
EP1543070A1 (de)	2005-06-22	Flammgeschützte styrolharzzusammensetzung
JP2002003727A (ja)	2002-01-09	難燃性樹脂組成物
EP2743308B1 (de)	2016-10-26	Flammschutzmittel und flammwidrige zusammensetzung für styrolharze
KR100187459B1 (ko)	1999-05-15	저광택 난연 수지 조성물
EP0520095A1 (de)	1992-12-30	Flammhemmende Harzmischung
JPH0344106B2 (de)	1991-07-04
KR101534954B1 (ko)	2015-07-24	비할로겐 난연 스티렌계 수지 조성물
WO1991006598A1 (en)	1991-05-16	Ignition resistant carbonate polymer blend compositions
CA1167193A (en)	1984-05-08	Flame retardant, styrene-grafted polyphenylene ether resin composition containing a phosphine oxide
EP0523790B1 (de)	1997-10-01	Flammgeschützte thermoplastische Zusammensetzung
KR101769185B1 (ko)	2017-08-17	열가소성 수지 조성물
JP3563630B2 (ja)	2004-09-08	難燃性スチレン系樹脂組成物
JPH0798891B2 (ja)	1995-10-25	高耐光性難燃樹脂組成物
KR100782698B1 (ko)	2007-12-07	난연성 스티렌계 수지 조성물
JPS62143961A (ja)	1987-06-27	耐熱性の優れた難燃性樹脂組成物

Legal Events

Date	Code	Title	Description
1997-10-21	MKEX	Expiry