NL8006914A - Fosforderivaten 1,3-diethanolureum en daaruit bereide polyurethanharsen. - Google Patents

Fosforderivaten 1,3-diethanolureum en daaruit bereide polyurethanharsen. Download PDF

Info

Publication number: NL8006914A
Authority: NL; Netherlands
Prior art keywords: compounds; covalent bond; flame; polyurethane resin; represent
Prior art date: 1980-03-24

Application number

NL8006914A

Other languages

English (en)

Dutch (nl)

Original Assignee

Pennwalt Corp

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.)

1980-03-24

Filing date

1980-12-19

Publication date

1981-10-16

1980-12-19 Application filed by Pennwalt Corp filed Critical Pennwalt Corp

1981-10-16 Publication of NL8006914A publication Critical patent/NL8006914A/nl

Links

229920002635 polyurethane Polymers 0.000 title description 12
150000003017 phosphorus Chemical class 0.000 title description 5
229920005989 resin Polymers 0.000 title description 3
239000011347 resin Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 40
239000003063 flame retardant Substances 0.000 claims description 21
-1 flame retardant compound Chemical class 0.000 claims description 14
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 claims description 13
229910052698 phosphorus Inorganic materials 0.000 claims description 12
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
239000011574 phosphorus Substances 0.000 claims description 11
229920005749 polyurethane resin Polymers 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
229920001228 polyisocyanate Polymers 0.000 claims description 3
239000005056 polyisocyanate Substances 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000004814 polyurethane Substances 0.000 description 11
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
239000000779 smoke Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000006260 foam Substances 0.000 description 8
239000004202 carbamide Substances 0.000 description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 4
QFUVURAMXUMLLT-UHFFFAOYSA-N CCO.CCO.NC(N)=O Chemical compound CCO.CCO.NC(N)=O QFUVURAMXUMLLT-UHFFFAOYSA-N 0.000 description 3
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000002485 combustion reaction Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
150000003018 phosphorus compounds Chemical class 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 3
TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
OIERWUPLBOKSRB-UHFFFAOYSA-N dimethoxyphosphorylmethanol Chemical compound COP(=O)(CO)OC OIERWUPLBOKSRB-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 2
239000003039 volatile agent Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
NJLHHACGWKAWKL-UHFFFAOYSA-N ClP(Cl)=O Chemical class ClP(Cl)=O NJLHHACGWKAWKL-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
VTUOGCGFAYXLOX-UHFFFAOYSA-N NCOP(=O)OCCO Chemical compound NCOP(=O)OCCO VTUOGCGFAYXLOX-UHFFFAOYSA-N 0.000 description 1
RAGQVGHCFYRJNO-UHFFFAOYSA-N P(OCCO)(OCCN)=O Chemical compound P(OCCO)(OCCN)=O RAGQVGHCFYRJNO-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229920005830 Polyurethane Foam Polymers 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
CVNMBKFJYRAHPO-UHFFFAOYSA-N [chloro(methyl)phosphoryl]methane Chemical compound CP(C)(Cl)=O CVNMBKFJYRAHPO-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000000123 paper Substances 0.000 description 1
150000008298 phosphoramidates Chemical class 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011496 polyurethane foam Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000010791 quenching Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000004753 textile Substances 0.000 description 1
229920002803 thermoplastic polyurethane Polymers 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
QYRVVCYHGWGULA-UHFFFAOYSA-N tris(1,3-dichloropropyl) phosphite Chemical compound ClCCC(Cl)OP(OC(Cl)CCCl)OC(Cl)CCCl QYRVVCYHGWGULA-UHFFFAOYSA-N 0.000 description 1
FCFIEBVTVHJMQR-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphite Chemical compound ClCC(Cl)COP(OCC(Cl)CCl)OCC(Cl)CCl FCFIEBVTVHJMQR-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- 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
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5353—Esters of phosphonic acids containing also nitrogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polyurethanes Or Polyureas (AREA)
Fireproofing Substances (AREA)

NL8006914A 1980-03-24 1980-12-19 Fosforderivaten 1,3-diethanolureum en daaruit bereide polyurethanharsen. NL8006914A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/133,297 US4299782A (en)	1980-03-24	1980-03-24	Phosphorus derivatives of 1,3-diethanolurea
US13329780		1980-03-24

Publications (1)

Publication Number	Publication Date
NL8006914A true NL8006914A (nl)	1981-10-16

Family

ID=22457911

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8006914A NL8006914A (nl)	1980-03-24	1980-12-19	Fosforderivaten 1,3-diethanolureum en daaruit bereide polyurethanharsen.

Country Status (9)

Country	Link
US (1)	US4299782A (fr)
JP (1)	JPS56145294A (fr)
BE (1)	BE888081A (fr)
CA (1)	CA1159846A (fr)
DE (1)	DE3111565A1 (fr)
FR (1)	FR2478642A1 (fr)
GB (1)	GB2072678A (fr)
IT (1)	IT1170606B (fr)
NL (1)	NL8006914A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4405355A (en) *	1979-08-20	1983-09-20	Chevron Research Company	N-Alkyl or alkoxy-N'-substituted hydrocarbyl urea
CN112442074A (zh) *	2019-08-28	2021-03-05	广东广山新材料股份有限公司	一种反应型阻燃剂及其制备方法和应用
CN112442162A (zh) *	2019-08-28	2021-03-05	广东广山新材料股份有限公司	一种带有羟基的含磷阻燃剂及其制备方法和应用
CN112442076A (zh) *	2019-08-28	2021-03-05	广东广山新材料股份有限公司	一种反应型阻燃剂及其制备方法和应用
CN112442161A (zh) *	2019-08-28	2021-03-05	广东广山新材料股份有限公司	一种反应型阻燃剂及其制备方法和应用
CN112442077A (zh) *	2019-08-28	2021-03-05	广东广山新材料股份有限公司	一种带有反应基团的含磷阻燃剂及其制备方法和应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3763281A (en) *	1970-06-26	1973-10-02	Stauffer Chemical Co	Ureidoalkylphosphonates
GB1429004A (en) *	1972-03-30	1976-03-24	Hooker Chemicals Plastics Corp	Phosphonate esters useful as fire retardant additives
US3954860A (en) *	1973-08-06	1976-05-04	Monsanto Company	Phosphorous compounds
US3920733A (en) *	1973-08-06	1975-11-18	Monsanto Co	Ureidoalkylphosphonic acids
US3992294A (en) *	1974-01-07	1976-11-16	Hooker Chemicals & Plastics Corporation	Process for sequestering metal ions
US4055591A (en) *	1974-01-07	1977-10-25	Hooker Chemicals & Plastics Corporation	Phosphonomethyl compounds
US4020679A (en) *	1975-08-13	1977-05-03	Automation Industries, Inc.	Sled for ultrasonic NDT system

1980
- 1980-03-24 US US06/133,297 patent/US4299782A/en not_active Expired - Lifetime
- 1980-12-02 CA CA000365937A patent/CA1159846A/fr not_active Expired
- 1980-12-05 GB GB8039107A patent/GB2072678A/en not_active Withdrawn
- 1980-12-19 NL NL8006914A patent/NL8006914A/nl not_active Application Discontinuation
1981
- 1981-01-07 IT IT47525/81A patent/IT1170606B/it active
- 1981-01-12 FR FR8100383A patent/FR2478642A1/fr not_active Withdrawn
- 1981-03-12 JP JP3469581A patent/JPS56145294A/ja active Pending
- 1981-03-23 BE BE0/204225A patent/BE888081A/fr unknown
- 1981-03-24 DE DE19813111565 patent/DE3111565A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
IT1170606B (it)	1987-06-03
BE888081A (fr)	1981-07-16
GB2072678A (en)	1981-10-07
CA1159846A (fr)	1984-01-03
FR2478642A1 (fr)	1981-09-25
IT8147525A0 (it)	1981-01-07
JPS56145294A (en)	1981-11-11
US4299782A (en)	1981-11-10
DE3111565A1 (de)	1982-05-27

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1985-08-01	BV	The patent application has lapsed

Publication	Publication Date	Title
CA1236621A (fr)	1988-05-10	Composition ignifuge
US2891915A (en)	1959-06-23	Organophosphorus polymers
US4093641A (en)	1978-06-06	Preparation of silylalkyl esters of phosphorus
CN101333231B (zh)	2012-02-08	具有磷酸酯-膦酸酯键的有机磷化合物、及使用其的阻燃性纤维、组合物
NL8006914A (nl)	1981-10-16	Fosforderivaten 1,3-diethanolureum en daaruit bereide polyurethanharsen.
US3609107A (en)	1971-09-28	Self-extinguishing polyurethane foams
CA1273358A (fr)	1990-08-28	Agents d'ignifugation pour polyurethanes
US3968188A (en)	1976-07-06	Process for preparing the pentaerythritol ester of phosphorohalidous acid
US3970726A (en)	1976-07-20	Polycyclic phosphate esters and process for preparing same
US4052487A (en)	1977-10-04	Diol-phosphonates
US3639532A (en)	1972-02-01	Esters and/or amides of acids of phosphorus containing a group having the formula roch2nhco-
US4024207A (en)	1977-05-17	Diethyl hydroxymethylphosphonate esters, their preparation and use
CN105820586B (zh)	2018-12-14	含羟基聚(亚烷基磷酸酯)
US4172863A (en)	1979-10-30	Halogen-containing phosphates
US4083826A (en)	1978-04-11	Polymeric compositions containing a flame retardant amount of a bis(2,3-dibromopropyl)-chloroalkyl phosphate
US4307221A (en)	1981-12-22	Fire-resistant (co)polycarbonates containing alkaline diesters or hemiesters of phosphonic acids
WO1994021724A1 (fr)	1994-09-29	Composes ignifuges contenant du phosphore
US2728806A (en)	1955-12-27	Phosphorus modified halogenated hydrocarbons
US3440222A (en)	1969-04-22	Flame resistant phosphoramidate-polyester reaction products
US4054543A (en)	1977-10-18	Phosphorus-containing polyols as flame retardant agents for polyurethanes
US3699188A (en)	1972-10-17	Fire resistant polymers
GB2126233A (en)	1984-03-21	a process for the preparation of halogenated benzylphosphonic esters
US3742095A (en)	1973-06-26	Hydroxyalkylcarbamylalkylphosphonates
GB2126232A (en)	1984-03-21	A process for producing halogenated benzylphosphonic esters
US4242288A (en)	1980-12-30	Halogenated triphosphates