GB966525A - Compounds containing phosphorus - Google Patents
Compounds containing phosphorusInfo
- Publication number
- GB966525A GB966525A GB1367960A GB1367960A GB966525A GB 966525 A GB966525 A GB 966525A GB 1367960 A GB1367960 A GB 1367960A GB 1367960 A GB1367960 A GB 1367960A GB 966525 A GB966525 A GB 966525A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- rnp
- nco
- hydrazine
- ammonia
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 4
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 4
- 239000011574 phosphorus Substances 0.000 title abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 12
- -1 triethylamine Chemical class 0.000 abstract 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 9
- 125000003277 amino group Chemical group 0.000 abstract 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 229910021529 ammonia Inorganic materials 0.000 abstract 6
- 239000004753 textile Substances 0.000 abstract 6
- 239000007795 chemical reaction product Substances 0.000 abstract 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 abstract 4
- 229920000642 polymer Polymers 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical compound N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 abstract 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 3
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 3
- AJEUQEGGIWRKPT-UHFFFAOYSA-L [acetyloxy(dibutoxy)stannyl] acetate Chemical compound CCCCO[Sn](OC(C)=O)(OC(C)=O)OCCCC AJEUQEGGIWRKPT-UHFFFAOYSA-L 0.000 abstract 3
- 239000000654 additive Substances 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 abstract 3
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 150000004679 hydroxides Chemical class 0.000 abstract 3
- 239000012948 isocyanate Substances 0.000 abstract 3
- 150000002513 isocyanates Chemical class 0.000 abstract 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 3
- 229910000077 silane Inorganic materials 0.000 abstract 3
- 150000003512 tertiary amines Chemical class 0.000 abstract 3
- 239000008096 xylene Substances 0.000 abstract 3
- 238000009835 boiling Methods 0.000 abstract 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004327 boric acid Substances 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- LQNMKGMAEMEZHO-UHFFFAOYSA-N boric acid phenylboronic acid Chemical compound C1(=CC=CC=C1)B(O)O.B(O)(O)O LQNMKGMAEMEZHO-UHFFFAOYSA-N 0.000 abstract 1
- 230000008676 import Effects 0.000 abstract 1
- 239000000047 product Substances 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/776—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/28—Titanium compounds
-
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- 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
-
- 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)]
- C07F9/36—Amides thereof
-
- 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)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4484—Compounds containing the structure C-P(=X)(N-acyl)-X, C-P(=X)(N-heteroatom)-X or C-P(=X)(N-CN)-X (X = O, S, Se)
- C07F9/4492—Compounds containing the structure P(=X)(N-C(=X)-) (X = O, S, Se)
-
- 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
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
-
- 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
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
- C08G18/3861—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur containing sulfonamide and/or sulfonylhydrazide groups
-
- 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
-
- 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
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- 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
- C08G18/3897—Low-molecular-weight compounds having heteroatoms other than oxygen containing heteroatoms other than oxygen, halogens, nitrogen, sulfur, phosphorus or silicon
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)
- Crystallography & Structural Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
A process for making novel phosphorus compounds comprises reacting under anhydrous conditions an isocyanate of phosphorus having the general formula RnP(NCO)3-n or RnP(O)(NCO)3n in which R is ethyl, isopropyl or a phenyl radical and n is 0, 1 or 2, with a compound, the molecule of which contains one or more reactive hydrogen atoms in hydroxyl or amino groups directly attached to an atom other than carbon. The reaction may be carried out in ether, benzene, xylene, or aceto-nitrile in the presence, if desired, of a catalyst chosen from tertiary amines, e.g. triethylamine, or organotin compounds, e.g. dibutoxy tin diacetate, at a temperature up to the boiling-point of the medium. The compounds containing amino groups are specified as ammonia, hydrazine, phosphoryl triamide, sulphuryl amide, and dibutoxy silane diamine; whilst those containing OH groups are given as "o" phosphoric acid, diethylphosphite, phenyl phosphonic acid, boric acid, phenyl boronic acid, substituted silane diols and the hydroxides of Ca, Mg, Zn, Al and Mo. When the compounds are polyfunctional, i.e. contain more than one NH2 or OH group then the reaction product can be polymeric. The polymers obtained using the inorganic NH2 compounds, e.g. ammonia and hydrazine, may be further cross-linked with formaldehyde to give textile additives which impart flame resistance to the textile.ALSO:A process for making novel phosphorus compounds comprises reacting under anhydrous conditions an isocyanate of phosphorus having the general formula: RnP(NCO)3-n or RnP(O)(NCO)3-n in which R is an ethyl, isopropyl or a phenyl radical and n is 0, 1 or 2, with a compound, the molecule of which contains one or more reactive hydrogen atoms in hydroxyl or amino groups directly attached to an atom other than carbon. The reaction may be carried out in ether, benzene, xylene or aceto-nitrile in the presence, if desired, of a catalyst chosen from tertiary amines, e.g. triethylamine, or organo-tin compounds, e.g. dibutoxy tin diacetate, at a temperature up to the boiling point of the medium. The compounds containing amino groups are specified as ammonia, hydroxylamine, hydrazine, phosphoryl triamide, sulphuryl amide, and dibutoxy silane diamine; whilst those containing -OH groups are given as o phosphoric acid, diethyl phosphite, phenyl phosphonic acid, boric acid phenyl boronic acid, substituted silane diols and the hydroxides of Ca, Mg, Zn, Al and Mo. When the compounds are polyfunctional, i.e. contain more than one NH2 or OH group then the reaction product can be polymeric. Some of the products of the above reaction are claimed. The polymers obtained using the inorganic NH2 compounds, e.g. hydrazine and ammonia, may be further cross linked with formaldehyde to give textile additives which impart flame resistance to the textile.ALSO:A process for making novel phosphorus compounds, which may be polymers, comprises reacting under anhydrous conditions an isocyanate of phosphorus having the general formula RnP(NCO)3-n or RnP(O) (NCO)3-n in which R is an ethyl, isopropyl or a phenyl radical and n is 0, 1 or 2, with a compound, the molecule of which contains one or more reactive hydrogen atoms in hydroxyl or amino groups directly attached to an atom other than carbon. The reaction may be carried out in ether, benzene, xylene or acetonitrile in the presence, if desired, of a catalyst chosen from tertiary amines, e.g. triethylamine, or organo tin compounds, e.g. dibutoxy tin diacetate, at a temperature up to the boiling point of the medium. The compounds containing amino groups are specified as ammonia, hydrazine, phosphoryl triamide, sulphonyl amide and dibutoxy silane diamine; whilst those containing OH groups are given as o1phosphoric acid, diethylphosphite, phenyl phosphonic acid, boric acid, phenyl boronic acid, substituted silane diols and the hydroxides of Ca, Mn, Zn, Al and Mo. When the compounds are polyfunctional, i.e. contain more than one NH2 or OH group, then the reaction product may be polymeric, Certain of the polymeric reaction products are claimed, The polymers obtained using inorganic NH2 compounds e.g. ammonia and hydrazine, may be further cross-linked with formaldehyde to give textile additives which import flame resistance to the textile.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1367960A GB966525A (en) | 1960-04-19 | 1960-04-19 | Compounds containing phosphorus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1367960A GB966525A (en) | 1960-04-19 | 1960-04-19 | Compounds containing phosphorus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB966525A true GB966525A (en) | 1964-08-12 |
Family
ID=10027436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1367960A Expired GB966525A (en) | 1960-04-19 | 1960-04-19 | Compounds containing phosphorus |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB966525A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117843678A (en) * | 2023-12-29 | 2024-04-09 | 珠海宏昌电子材料有限公司 | Diisocyanate monomer and preparation method and application thereof |
-
1960
- 1960-04-19 GB GB1367960A patent/GB966525A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117843678A (en) * | 2023-12-29 | 2024-04-09 | 珠海宏昌电子材料有限公司 | Diisocyanate monomer and preparation method and application thereof |
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