GB991799A - The production of polyurethanes from hydroxyl-containing phosphonic acid esters containing nitrogen - Google Patents
The production of polyurethanes from hydroxyl-containing phosphonic acid esters containing nitrogenInfo
- Publication number
- GB991799A GB991799A GB16013/62A GB1601362A GB991799A GB 991799 A GB991799 A GB 991799A GB 16013/62 A GB16013/62 A GB 16013/62A GB 1601362 A GB1601362 A GB 1601362A GB 991799 A GB991799 A GB 991799A
- Authority
- GB
- United Kingdom
- Prior art keywords
- atoms
- phosphite
- radicals
- radical
- reacting
- Prior art date
- 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
Links
- 239000004814 polyurethane Substances 0.000 title abstract 10
- 229920002635 polyurethane Polymers 0.000 title abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title abstract 8
- 238000004519 manufacturing process Methods 0.000 title abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 title abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title 2
- 150000003008 phosphonic acid esters Chemical class 0.000 title 1
- -1 cycloaliphatic Chemical group 0.000 abstract 22
- 239000005056 polyisocyanate Substances 0.000 abstract 14
- 229920001228 polyisocyanate Polymers 0.000 abstract 13
- 150000003254 radicals Chemical class 0.000 abstract 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 9
- 125000002947 alkylene group Chemical group 0.000 abstract 8
- 239000004215 Carbon black (E152) Substances 0.000 abstract 7
- 229930195733 hydrocarbon Natural products 0.000 abstract 7
- 239000000047 product Substances 0.000 abstract 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 6
- 229910052698 phosphorus Inorganic materials 0.000 abstract 6
- 239000011574 phosphorus Substances 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 abstract 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 abstract 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 4
- 229940043237 diethanolamine Drugs 0.000 abstract 4
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 229920000768 polyamine Polymers 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 3
- 125000000732 arylene group Chemical group 0.000 abstract 3
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 abstract 3
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 3
- 230000001413 cellular effect Effects 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000007795 chemical reaction product Substances 0.000 abstract 3
- 239000008199 coating composition Substances 0.000 abstract 3
- 125000004982 dihaloalkyl group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 125000004957 naphthylene group Chemical group 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 3
- 125000001918 phosphonic acid ester group Chemical group 0.000 abstract 3
- 229920000728 polyester Polymers 0.000 abstract 3
- 150000005846 sugar alcohols Polymers 0.000 abstract 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 abstract 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 2
- 239000001361 adipic acid Substances 0.000 abstract 2
- 235000011037 adipic acid Nutrition 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000006229 carbon black Substances 0.000 abstract 2
- 239000011248 coating agent Substances 0.000 abstract 2
- 238000000576 coating method Methods 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 229920001971 elastomer Polymers 0.000 abstract 2
- 229920006248 expandable polystyrene Polymers 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 2
- 239000000123 paper Substances 0.000 abstract 2
- 239000000049 pigment Substances 0.000 abstract 2
- 229920003023 plastic Polymers 0.000 abstract 2
- 239000004033 plastic Substances 0.000 abstract 2
- 239000005060 rubber Substances 0.000 abstract 2
- VVNRQZDDMYBBJY-UHFFFAOYSA-M sodium 1-[(1-sulfonaphthalen-2-yl)diazenyl]naphthalen-2-olate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 VVNRQZDDMYBBJY-UHFFFAOYSA-M 0.000 abstract 2
- 239000004408 titanium dioxide Substances 0.000 abstract 2
- 125000005628 tolylene group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002023 wood Substances 0.000 abstract 2
- 239000008096 xylene Substances 0.000 abstract 2
- 239000011787 zinc oxide Substances 0.000 abstract 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 abstract 1
- UGXAIVCNTXGYSA-UHFFFAOYSA-N 2,2,2-trichloroethyl dihydrogen phosphite Chemical compound OP(O)OCC(Cl)(Cl)Cl UGXAIVCNTXGYSA-UHFFFAOYSA-N 0.000 abstract 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004604 Blowing Agent Substances 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 abstract 1
- 239000004150 EU approved colour Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- DMGNFLJBACZMRM-UHFFFAOYSA-N O[P] Chemical class O[P] DMGNFLJBACZMRM-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 abstract 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 abstract 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 abstract 1
- JZPCVNQVJCFHOZ-UHFFFAOYSA-N dichloro ethyl phosphite Chemical compound CCOP(OCl)OCl JZPCVNQVJCFHOZ-UHFFFAOYSA-N 0.000 abstract 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 abstract 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 abstract 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000004872 foam stabilizing agent Substances 0.000 abstract 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 239000011874 heated mixture Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 abstract 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 abstract 1
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 abstract 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 abstract 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 1
- 229920001281 polyalkylene Polymers 0.000 abstract 1
- 229920006324 polyoxymethylene Polymers 0.000 abstract 1
- 229920006295 polythiol Polymers 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229920002545 silicone oil Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 235000011150 stannous chloride Nutrition 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 150000003606 tin compounds Chemical class 0.000 abstract 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 abstract 1
- 229940029284 trichlorofluoromethane Drugs 0.000 abstract 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
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3889—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having nitrogen in addition to phosphorus
-
- 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
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention comprises polyhydroxyl compounds containing phosphonic acid ester groups and nitrogen atoms which are obtainable by condensing a primary or secondary aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic mono- and/or polyamine containing at least one hydrogen atom attached to the amino nitrogen atom and also containing at least two hydroxyl groups with an organic carbonyl compound and a dialkyl or dihaloalkyl or dicycloalkyl phosphite. Preferred polyhydroxyl products are those having the general formula <FORM:0991799/C2/1> in which R and R1 are hydrogen atoms or hydrocarbon radicals which may be substituted by halogen atoms, R11 is a C1-C18 alkyl radical haloalkyl or cycloalkyl radical, X, Y and Z are each alkylene, arylene or aralkylene radicals which may be the same or different and may be interrupted by hetero atoms (e.g. by -O-, -S- or -N- atoms) and/or contain free OH groups and m is O or an integer from 1 to 10. Z may be the same radical as X or Y and may conveniently be an alkylene or aralkylene radical containing 2 to 12 carbon atoms or an arylene radical containing one or two benzene rings such as phenylene, naphthylene, diphenylene or tolylene. R and R1 when they are hydrocarbon radicals can be alkyl, alkenyl, cycloalkyl, cyclo-alkyl substituted alkenyl radicals, aralkyl or aralkenyl radicals and several suitable radicals of each type and of halogen-substituted hydrocarbon radicals are specified. The reaction can be effected by simple mixing of the reactants preferably at 20 DEG to 100 DEG C. The products can be used directly for reaction with organic polyisocyanates to form polyurethane plastics (see Divisions B2 and C3), or can be modified beforehand by reacting with alkylene oxides, e.g. ethylene-, propylene- or butylene oxide, epichlorhydrin or styrene oxide. The products may have a molecular weight of from 200 to 10,000 and an OH number of 40 to 800. Examples are given for the production of polyhydroxy compounds from (1) and (2) formaldehyde, diethyl (or dimethyl) phosphite and diethanolamine, (3) and (4) formaldehyde, diethyl (or dimethyl) phosphite and N,N,N1 - tris - (beta - hydroxypropyl) - ethylene diamine, (5) formaldehyde, diethyl phosphite and the product obtained by reacting 2,4-diamino toluene in ethanol with ethylene oxide, (6) formaldehyde, dimethyl phosphite and N,N1 - di - (beta - hydroxypropyl) - ethylene diamine, (7) formaldehyde, diethyl phosphite and a product obtained by reacting a mixture of pentaethylene hexamine and a small amount of water with propylene oxide, (8), (9) and (10) crotonaldehyde (acetaldehyde or iso-butyraldehyde), diethyl phosphite and diethanolamine, (11) cyclohexanone, diethyl phosphite and diethanolamine, and (12) formaldehyde, diethanol-amine and dichloroethyl phosphite.ALSO:Polyurethanes are obtained by reacting organic polyisocyanates with polyhydroxyl compounds containing phosphonic acid ester groups and nitrogen atoms and which are obtainable by condensing a primary or secondary aliphatic, cyclo-aliphatic, aromatic, araliphatic or heterocyclic mono- and/or polyamine containing at least one hydrogen atom attached to the amino nitrogen atom and also containing at least two hydroxyl groups with an organic carbonyl compound and a dialkyl or dihaloalkyl or dicycloalkyl phosphite (see Division C2). Preferred polyhydroxyl products are those having the general formula <FORM:0991799/C3/1> in which R and R1 are hydrogen atoms or hydrocarbon radicals which may be substituted by halogen atoms, R11 is a C1-C18 alkyl radical haloalkyl or cycloalkyl radical, X, Y and Z are each alkylene, arylene or aralkylene radicals which may be the same or different and may be interrupted by hetero atoms (e.g. by -O-, -S- or -N- atoms) and/or contain free OH groups and m is 0 or an integer from 1 to 10. Z may be the same radical as X or Y and may conveniently be an alkylene or aralkylene radical containing 2 to 12 carbon atoms or an arylene radical containing one or two benzene rings such as phenylene, naphthylene, diphenylene or tolylene. R and R1 when they are hydrocarbon radicals can be alkyl, alkenyl, cycloalkyl, cycloalkyl substituted alkenyl radicals, aralkyl or aralkenyl radicals and several suitable radicals of each type and of halogen-substituted hydrocarbon radicals are specified. The polyhydroxy phosphorus compounds can be modified by reacting with alkylene oxides, e.g. ethylene-, propylene- or butylene oxide, epichlorhydrin or styrene oxide, before reacting with the organic polyisocyanate to form the polyurethanes. The organic polyisocyanates may be aromatic, aliphatic (including cycloaliphatic) or heterocyclic polyisocyanates and include a phosphorus-containing polyisocyanate and several suitable compounds are specified including di- and poly-isocyanates, e.g. p,p1,p11-triisocyanato phenyl phosphate. It is preferred to use aromatic polyisocyanates, e.g. a mixture of toluylene diisocyanates; diphenylmethane-4,41 diisocyanate and the crude isocyanates obtained by phosgenation of the reaction product of aniline and formaldehyde or of a mixture of meta- and para-toluylene diamines. The hydroxyl phosphorus compounds may be used in conjunction with a compound containing active hydrogen containing groups, as determined by the Zerewitinoff method, e.g. polyhydric polyalkylene ethers, hydroxy polyesters (e.g. the reaction product of a polycarboxylic acid with a polyhydric alcohol), polyhydric polythioethers, polyacetals, e.g. the reaction product of a polyhydric alcohol with an aldehyde, e.g. formaldehyde, and propoxylated phosphoric acid. Cellular polyurethanes are obtained by carrying out the reaction in the presence of a blowing agent, e.g. a halohydrocarbon such as dichlorodifluoromethane or trichlorofluoromethane or by using water and sufficient excess of the polyisocyanate to produce carbon dioxide. Other additives may also be present, e.g. emulsifiers such as sulphonated castor oil, foam stabilizers, e.g. a silicone oil, colouring agents and/or fillers. A catalyst may also be present, e.g. a tertiary amine, a tin compound, e.g. stannous chloride or a tin salt of a carboxylic acid, or other metal organic compounds. Non-porous polyurethanes may be obtained by reacting an excess of the organic polyisocyanate with the phosphorus compound and an organic cross-linking agent, e.g. a polyhydric alcohol, a polyamine or hydroxyamine under substantially anhydrous conditions. A coating composition may be obtained by reacting the polyisocyanate and the phosphorus compound in an inert organic solvent, e.g. xylene, toluene, ethyl acetate, diethyl ether of ethylene glycol, or ethylene glycol monoethyl ether monoacetate and such coating compositions may be used for coating wood, paper, sponge rubber, cellular polyurethanes, or foamed polystyrene and such compositions may contain a pigment or dye-stuff, e.g. iron oxide, carbon black, titanium dioxide, zinc oxide, chrome green or lithol red. Several examples are given for the production of foamed polyurethanes. An example is also given for the production of a non-foamed polyurethane in which example a polyester prepared from adipic acid and ethylene glycol is chain extended with toluylene diisocyanate, dissolved in ethyl acetate and mixed with a phosphorus compound of the formula <FORM:0991799/C3/2> a phosphorus and chlorine-containing polyisocyanate (prepared as below) and a diurethane obtained from 1 mol. of N-methyl diethanolamine and 2 mols. of phenyl isocyanate and the resulting solution is applied several times to each side of a cotton fabric which is then dried at about 80 DEG C. after each coat, the resulting coated fabric being flameproof. The phosphorus-containing polyisocyanate is obtained by adding phosgene to a residue obtained by distilling off a mixture of cyclohexylisocyanate and hexamethylene diisocyanate from a heated mixture of hexamethylene diisocyanate and cyclohexyl carbodiimide and then reacting with trichloroethyl phosphite at 90-100 DEG C., with elimination of ethylene chloride. Specifications 769,682, 804,369 and 819,384 are referred to.ALSO:A coating composition is obtained by reacting in an inert organic solvent an organic polyisocyanate with a polyhydroxyl compound containing phosphonic acid ester groups and nitrogen atoms which is obtainable by condensing a primary or secondary aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic mono- and/or polyamine containing at least one hydrogen atom attached to the amino nitrogen atom and also containing at least two hydroxyl groups with an organic carbonyl compound and a dialkyl or dihaloalkyl or dicycloalkyl phosphite (see Division C2). Preferred polyhydroxyl products are those having the general formula <FORM:0991799/B1-B2/1> in which R and R1 are hydrogen atoms or hydrocarbon radicals which may be substituted by halogen atoms, R11 is a C1-C18 alkyl radical, haloalkyl or cycloalkyl radical, X, Y and Z are each alkylene, arylene or aralkylene radicals which may be the same or different and may be interrupted by hetero atoms (e.g. by -O-, -S- or -N- atoms) and/or contain free OH groups and m is 0 or an integer from 1 to 10. Z may be the same radical as X or Y and may conveniently be an alkylene or aralkylene radical containing 2-12 carbon atoms or an arylene radical containing one or two benzene rings such as phenylene, naphthylene, diphenylene or tolulene. The inert organic solvent may be xylene, toluene, ethylene glycol diethyl ether, ethyl acetate or ethylene glycol monoethyl ether monoacetate. The composition may contain a pigment or dyestuff, e.g. iron oxide, carbon black, titanium dioxide, zinc oxide, chrome green or lithol red, and is suitable for coating wood, paper, rubber, metal, cellular polyurethane plastics and foamed polystyrene. In an example a polyester prepared from adipic acid and ethylene glycol is chain-extended with toluyle
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF33811A DE1143022B (en) | 1961-04-29 | 1961-04-29 | Process for the production of flame-retardant plastics |
Publications (1)
Publication Number | Publication Date |
---|---|
GB991799A true GB991799A (en) | 1965-05-12 |
Family
ID=7095267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB16013/62A Expired GB991799A (en) | 1961-04-29 | 1962-04-26 | The production of polyurethanes from hydroxyl-containing phosphonic acid esters containing nitrogen |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE617051A (en) |
DE (1) | DE1143022B (en) |
GB (1) | GB991799A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20180223032A1 (en) * | 2015-08-18 | 2018-08-09 | Pcc Rokita Sa | Flame-resistant polymer polyol dispersion |
CN111056627A (en) * | 2018-10-17 | 2020-04-24 | 中电建生态环境集团有限公司 | Use method of biological aerated filter system for purifying black and odorous water body water quality |
CN112358502A (en) * | 2020-11-09 | 2021-02-12 | 山东省海洋化工科学研究院 | Double-hydroxyl high-phosphorus-nitrogen-content flame-retardant functional monomer and preparation method thereof |
CN112442161A (en) * | 2019-08-28 | 2021-03-05 | 广东广山新材料股份有限公司 | Reactive flame retardant and preparation method and application thereof |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3437607A (en) * | 1965-03-31 | 1969-04-08 | Upjohn Co | Polyurethane pre-mixes containing dihydroxy nitrogen containing phosphonates |
DE3025309A1 (en) | 1980-07-04 | 1982-02-04 | Bayer Ag, 5090 Leverkusen | If necessary, foamed intumescent measures |
DE3041731A1 (en) * | 1980-11-05 | 1982-06-09 | Bayer Ag, 5090 Leverkusen | If necessary, foamed intumescent materials and their use |
DE3528754A1 (en) * | 1985-08-10 | 1987-02-19 | Bayer Ag | METHOD FOR REDUCING THE FLAMMABILITY OF SUCTIONABLE SUBSTRATES, AND FLAME PROTECTED COVERINGS AND PACKAGING MATERIALS THEREOF |
DE3917518A1 (en) | 1989-05-30 | 1990-12-06 | Bayer Ag | FIRE PROTECTION ELEMENTS |
-
0
- BE BE617051D patent/BE617051A/xx unknown
-
1961
- 1961-04-29 DE DEF33811A patent/DE1143022B/en active Pending
-
1962
- 1962-04-26 GB GB16013/62A patent/GB991799A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20180223032A1 (en) * | 2015-08-18 | 2018-08-09 | Pcc Rokita Sa | Flame-resistant polymer polyol dispersion |
US11046807B2 (en) * | 2015-08-18 | 2021-06-29 | Pcc Rokita Sa | Flame-resistant polymer polyol dispersion |
CN111056627A (en) * | 2018-10-17 | 2020-04-24 | 中电建生态环境集团有限公司 | Use method of biological aerated filter system for purifying black and odorous water body water quality |
CN112442161A (en) * | 2019-08-28 | 2021-03-05 | 广东广山新材料股份有限公司 | Reactive flame retardant and preparation method and application thereof |
CN112358502A (en) * | 2020-11-09 | 2021-02-12 | 山东省海洋化工科学研究院 | Double-hydroxyl high-phosphorus-nitrogen-content flame-retardant functional monomer and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
DE1143022B (en) | 1963-01-31 |
BE617051A (en) |
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