US3687952A - HALOGENPHENOXY-s-TRIAZINE DERIVATIVES HAVING IMPROVED SOLUBILITY - Google Patents
HALOGENPHENOXY-s-TRIAZINE DERIVATIVES HAVING IMPROVED SOLUBILITY Download PDFInfo
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- US3687952A US3687952A US800699A US3687952DA US3687952A US 3687952 A US3687952 A US 3687952A US 800699 A US800699 A US 800699A US 3687952D A US3687952D A US 3687952DA US 3687952 A US3687952 A US 3687952A
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- Prior art keywords
- triazine
- alkyl
- carbon atoms
- halogenated
- reaction
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- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 4,6-di(2,4,6-trichlorophenoxy)-s-triazine Chemical compound 0.000 claims description 13
- CGQMBOJOSBBNNV-UHFFFAOYSA-N 2,4-bis(2,3,4,5,6-pentachlorophenoxy)-1,3,5-triazine Chemical compound ClC1=C(C(=C(C(=C1OC1=NC=NC(=N1)OC1=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)Cl)Cl)Cl)Cl CGQMBOJOSBBNNV-UHFFFAOYSA-N 0.000 claims description 3
- CHAHVQRPCWVQTH-UHFFFAOYSA-N 2,4-bis(2,3,4-tribromophenoxy)-1,3,5-triazine Chemical compound BrC1=C(Br)C(Br)=CC=C1OC1=NC=NC(OC=2C(=C(Br)C(Br)=CC=2)Br)=N1 CHAHVQRPCWVQTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 10
- 125000003118 aryl group Chemical group 0.000 abstract description 7
- 150000003839 salts Chemical class 0.000 abstract description 6
- 150000003918 triazines Chemical class 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- 239000002671 adjuvant Substances 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 3
- 150000001340 alkali metals Chemical class 0.000 abstract description 3
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000003063 flame retardant Substances 0.000 abstract description 3
- 230000000855 fungicidal effect Effects 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 231100000208 phytotoxic Toxicity 0.000 abstract description 3
- 230000000885 phytotoxic effect Effects 0.000 abstract description 3
- 239000004753 textile Substances 0.000 abstract description 3
- 239000003899 bactericide agent Substances 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 239000002917 insecticide Substances 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003008 phosphonic acid esters Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 description 1
- AYCYRPHLXAYENC-UHFFFAOYSA-N 2-chloro-4,6-bis(2,3,4,5,6-pentachlorophenoxy)-1,3,5-triazine Chemical compound N=1C(OC=2C(=C(Cl)C(Cl)=C(Cl)C=2Cl)Cl)=NC(Cl)=NC=1OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl AYCYRPHLXAYENC-UHFFFAOYSA-N 0.000 description 1
- YAMHDNBUUSFGGQ-UHFFFAOYSA-N 4-phenoxytriazine Chemical class C=1C=NN=NC=1OC1=CC=CC=C1 YAMHDNBUUSFGGQ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-VCOUNFBDSA-N Decaline Chemical compound C=1([C@@H]2C3)C=C(OC)C(OC)=CC=1OC(C=C1)=CC=C1CCC(=O)O[C@H]3C[C@H]1N2CCCC1 PXXNTAGJWPJAGM-VCOUNFBDSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6521—Six-membered rings
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
Definitions
- I kali metal or onium 3 is y g alkyl having [58] Field of Search ..260/248 CS, 249.5 two to '18 halogenated alkyl having two to 18 carbon atoms or cycloalkyl, and R is alkyl, [56] References Cited cycloalkyl, aryl, halogenated alkyl, halogenated UNITED STATES PATENTS cycloalkyl or halogenated aryl, and wherein R and R taken together with the nitrogen atom to which they 2 5 3: 31 121 21356 are attached form a heterocyclic ring.
- novel halophenoxy-s-triazine derivatives and salts are suita ble for use as water repellants, parting agents, textile adjuvants, as fire retardants, fungicidal, phytotoxic,
- R represents alkyl, halogenated alkyl, alkali metal, or ammonium
- R represents hydrogen, alkyl containing two to 18 carbon atoms, halogenated alkyl containing two to 18 carbon atoms or cycloalkyl
- R represents alkyl, containing two to 18 carbon atoms, halogenated alkyl containing two to 18 carbon atoms, cycloalkyl or aryl and wherein R and R taken together can form a heterocyclic ring.
- novel derivatives of the invention are characterized in that they are soluble in organic solvents.
- the highly chlorinated halogenphenoxy-s-triazines which have heretofore been available and particularly those containing the pentachlorophenoxy group, exhibit only a very slight solubility in organic solvents.
- the preparation of the new triazine compounds is carried out by reacting a halogenphenoxy-s-triazine with a phosphorus acid ester at a temperature between 50 C. and 250 C and preferably at a temperature of from C to 200 C.
- the re-esterification can be carried out both in the fused state and with an organic solvent.
- the reaction temperature is increased as the reaction proceeds so that the reaction mixture is constantly boiling.
- Alkyl halide is split off in the reaction, and the course of the reaction can be followed on the basis of the quantity of alkyl halide that is recovered.
- the reaction generally requires from 1 to 6 hours. After the evolution of alkyl halide has ended, the unreacted reactants are separated off by vacuum distillation. In most instances the distillation residue is analytically pure and requires no further purification measures.
- Aliphatic and aromatic hydrocarbons as well as simple and cyclic ethers are suitable as solvents for use in the reaction. It is advantageous to use not only the solvents in pure form, as for example, an aliphatic hydrocarbon compound such as isoctane, but also their mixtures can be used, such as benzine fractions, instance fractions having a boiling range of from to 200 C.
- Chlorinated hydrocarbons such as dichlorothane, tetrachlorethylene, and pentachlorethane, can also be used as solvents.
- Benzene, toluene, o-dichlorbenzene and xylene are examples of suitable aromatic hydrocarbons.
- suitable ethers include: diisopropyl ether, diisoamyl ether, diphenyl ether, 1,4-dioxane etc. The above enumeration is indicative of the fact that both aliphatic and aromatic open-chain ethers can be satisfactorily used.
- Polar solvents such as dimethylsulfoxide, dimethylformamide, the dimethyl ether of diethylene glycol, and decaline, have also been found to be useful as solvents.
- the starting materials for use in the process of the invention can be halogenated phenoxy-triazine derivatives containing reactive chlorine atoms, such as have been described in US. Pat. application Ser. No. 737129, now abandoned.
- the phosphorus acid esters which can be used in the reaction with the triazine derivatives include the trialkyl phosphites in general. Lower alkyl esters of phosphorus acid, such as triethyl phosphite, tripropyl phosphite, etc., are preferred for the reaction. Halogenated trialkylphosphites, such as tris-(B- chlorethyl)-phosphite can also be advantageously used in the reaction according to the invention.
- the saponification to form the salts is carried out by conventional methods, as for instance, by dissolving the phosphonic acid ester derivatives in organic solvents and heating them with an alkali.
- the organic solvents which can be used for dissolv- 5 ing the phosphonic acid ester derivatives include alcohols and ketones, as for example ethanol, acetone etc., as well as the solvents mentioned heretofore in connection with the reaction of the halogenphenoxy-striazines with alkyl phosphites.
- the reaction can be conducted either with the reactants in the fused state or in an inert solvent.
- the inert solvent then having the function both of a genuine solvent and of a dispersing agent.
- the solvents which have been enumerated as suitable for use in the reaction of the halogenphenoxy-s-triazine with phosphorus acid esters can also be used for the reaction with the amine Ra H--N/ .34.
- the catalysts for use in the reaction are tertiary amines having aliphatic, cycloaliphatic and aromatic radicals in which case the substituted imines are to be understood as constituting a type of cyclic tertiary amine.
- catalysts which may be used are acid amides or N-mono or disubstituted acid amides of monobasic, aliphatic, aromatic or araliphatic carboxylic acids having one to 18 carbon atoms. These acid amides have been described for instance in US. Pat. application Ser. No. 737,129, now abandoned.
- the amines used for the reaction themselves serve as reaction catalysts, so that the use of a special catalyst of the kind described above can in many instances be dispensed with.
- the new compounds and their salts can be used as water repellants, parting agents, dressings for glass fabrics, textile adjuvants, for the surface treatment of various materials and articles because of their fire-retardant, fungicidal, phytotoxic, bactericidal and insecticidal properties. They can also be used as additives for varnishes and enamels.
- EXAMPLE 1 2phosphonic acid diethy1ester,6-di-(trichlorophenoxy)-triazine 50.7 g of 2-chloro-4,6-di-(trichlorophenoxy)-striazine and 18.6 ml of triethylphosphite were weighed out and placed in a 250 ml 4-necked flask equipped with a stirrer, condenser, thermometer and a nitrogen gas introducing tube. The reaction mixture was slowly heated to 155 C and stirred for 2 hours at this temperature while being maintained under a current of nitrogen. The mixture was thereafter cooled to 120 C and the excess triethylphosphite removed by distillation in vacuo. The recovered product had a melting point of 74-78 C.
- the sodium salt of this compound was prepared as follows: 8 grams of the substance were dissolved in ml of acetone and then added under stirring to a sodium hydroxide solution in water (lgram/S ml H O). After 30 minutes stirring, the solution mixture was evaporated.
- EXAMPLE 3 2-[phosphonic acid di-(B-chlorethyD-ester]-4,6-di- (tetrachlorophenoxy)-triazine There were introduced into a 100 ml 4-neck flask provided with stirrer, condenser, thermometer, and nitrogen gas introduction tube, 28.8 g of 2-ch1oro-4,6- di-(tetrachloro-phenoxy)-s-triazine and 13.5 g of tris- B-chlorethylphosphite. While maintained under a current of nitrogen gas, the reaction mixture was slowly heated to 200 C and stirred at this temperature for 2 hours. The recovered product had a melting point of l l l-1 14 C.
- EXAMPLE 7 2-butylimino-4,6-di-(2,4,6-tribromophenoxy)-striazine
- 22.25 g of 2-chloro-4,6-di-(2,4,6-tribromophenoxy)-striazine were reacted with 2.2 g of n-butylamine and xylene as solvent.
- R represents a member selected from the group of wherein R represents a member of the group consisting of alkyl having one to five carbon atoms,- halogenated alkyl having one to five carbon atoms, alkali metal and ammonium, R is hydrogen or a two to 18 carbon atom member selected from the group consisting of alkyl, cycloalkyl and haloalkyl, and R is a two to 18 carbon atom member selected from the group consisting of alkyl, cycloalkyl, haloalkyl and carbocyclic aryl, wherein R and R taken together are alkylene and taken together with the nitrogen atom to which they are attached can also form a cycloalkylimino ring having no more than six carbon atoms,
- a compound according to claim 1 designated 2- I anilide, 4,6-di-(pentachlorophenoxy)-s-triazine.
- a compound according to claim 1 designated 2- anilide, 4,6-di-(tribromophenoxy )-s-triazine.
- a compound according to claim 1 designated 2- (2-ethylhexylimino)-4,6-di-(2,3,4,6- tetrachlorophenoxy)-s-triazine.
- a compound according to claim 1 designated 2- butylimino-4,6-di-(2,4,6-tribromophenoxy)-s-triazine.
- a compound according to claim 1 designated 2- di-( 2-ethylhexylimino)-4,6-di-(pentachlorophenoxy)- s-triazine.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Novel halophenoxy-s-triazine derivatives and salts thereof characterized by improved solubilities having the formula:-
WHEREIN X represents from one to five halogen atoms and R1 is either of
WHEREIN R2 is alkyl having one to five carbon atoms, halogenated alkyl having one to five carbon atoms, alkali metal or ammonium, R3 is hydrogen, alkyl having two to 18 carbon atoms, halogenated alkyl having two to 18 carbon atoms or cycloalkyl, and R4 is alkyl, cycloalkyl, aryl, halogenated alkyl, halogenated cycloalkyl or halogenated aryl, and wherein R3 and R4 taken together with the nitrogen atom to which they are attached form a heterocyclic ring. The novel triazine derivatives and their salts are suitable for use as water repellants, parting agents, textile adjuvants, as fire retardants, fungicidal, phytotoxic, bactericidal and insecticidal agents.
WHEREIN X represents from one to five halogen atoms and R1 is either of
WHEREIN R2 is alkyl having one to five carbon atoms, halogenated alkyl having one to five carbon atoms, alkali metal or ammonium, R3 is hydrogen, alkyl having two to 18 carbon atoms, halogenated alkyl having two to 18 carbon atoms or cycloalkyl, and R4 is alkyl, cycloalkyl, aryl, halogenated alkyl, halogenated cycloalkyl or halogenated aryl, and wherein R3 and R4 taken together with the nitrogen atom to which they are attached form a heterocyclic ring. The novel triazine derivatives and their salts are suitable for use as water repellants, parting agents, textile adjuvants, as fire retardants, fungicidal, phytotoxic, bactericidal and insecticidal agents.
Description
United States Patent Ismail Aug. 29, 1972 [54] HALOGENPHENOXY-S-TRIAZINE thereof characterized by improved solubilities having DERIVATIVES HAVING IMPROVED the formula:- SOLUBILITY 1 1 N [72] inventor: Roshdy Ismail, Rodderstrasse 6,
5213 Spich, Germany 1 [73] Assignee: Dynamit Nobel Aktiengesellschaft, I X \C/ X Troisdorf, Germany iii '1 d: F b. 19 l [22] e e 969 wherein X represents from one to five halogen atoms PP 800,699 and R is either of [30] Foreign Application Priority Data Feb. 21, 1968 Germany ..P 17 70 591.2 "fly May 31, 1968 Germany ..P 17 70 549.6
52 U.S. Cl. ..260/248 cs, 260/249.5, 260/999 wherein R2 is alkyl h1ving five carbm mm, [51] Int Cl and 55/50 halogenated alkyl having one to five carbon atoms, al-
I kali metal or onium, 3 is y g alkyl having [58] Field of Search ..260/248 CS, 249.5 two to '18 halogenated alkyl having two to 18 carbon atoms or cycloalkyl, and R is alkyl, [56] References Cited cycloalkyl, aryl, halogenated alkyl, halogenated UNITED STATES PATENTS cycloalkyl or halogenated aryl, and wherein R and R taken together with the nitrogen atom to which they 2 5 3: 31 121 21356 are attached form a heterocyclic ring.
Primary Examiner-John M. Ford Att0meyBurgess, Dinklage & Sprung [57] ABSTRACT Novel halophenoxy-s-triazine derivatives and salts The novel triazine derivatives and their salts are suita ble for use as water repellants, parting agents, textile adjuvants, as fire retardants, fungicidal, phytotoxic,
bactericidal and insecticidal agents.
10 Claims, No Drawings HALOGENPHENOXY-S-TRIAZINE DERIVATIVES Where, in the above set out formula R is HAVING IMPROVED SOLUBILITY This invention relates to halogenphenoxy-s-triazine derivatives having improved solubility characteristics.
According to the present invention there is provided a novel group of halogenphenoxy-s-triazine derivatives which have the formula:-
wherein X represents from one halogen or an amino group of the formula:-
in which R represents alkyl, halogenated alkyl, alkali metal, or ammonium, R represents hydrogen, alkyl containing two to 18 carbon atoms, halogenated alkyl containing two to 18 carbon atoms or cycloalkyl and R represents alkyl, containing two to 18 carbon atoms, halogenated alkyl containing two to 18 carbon atoms, cycloalkyl or aryl and wherein R and R taken together can form a heterocyclic ring.
The novel derivatives of the invention are characterized in that they are soluble in organic solvents. The highly chlorinated halogenphenoxy-s-triazines which have heretofore been available and particularly those containing the pentachlorophenoxy group, exhibit only a very slight solubility in organic solvents.
In accordance with the invention it has been found that the solubility in organic solvents is considerably improved by replacing the halogen atoms in carbonhalogenated halogenphenoxy-s-triazines, i.e., those which still contain reactive halogen atoms, with the above-defined moiety R Thus for example, 2-chloro- 4,6-di-(pentachlorophenoxy)-s-triazine, which has a melting point of 327 C is substantially insoluble in nearly all organic solvents, while 2-phosphonic acid diethylester4,6-di-(pentachlorophenoxy)-s-triazine is readily soluble in aromatic and chlorinated hydrocarbons. This can be seen from the following Table. The compatibility of the triazine compounds with aromatic solvents is of great importance in practice.
Comparison of solubility in various organic solvents at 25C of compounds a and b in grams per 100 milliliters.
the preparation of the new triazine compounds is carried out by reacting a halogenphenoxy-s-triazine with a phosphorus acid ester at a temperature between 50 C. and 250 C and preferably at a temperature of from C to 200 C. The re-esterification can be carried out both in the fused state and with an organic solvent. The reaction temperature is increased as the reaction proceeds so that the reaction mixture is constantly boiling. Alkyl halide is split off in the reaction, and the course of the reaction can be followed on the basis of the quantity of alkyl halide that is recovered. The reaction generally requires from 1 to 6 hours. After the evolution of alkyl halide has ended, the unreacted reactants are separated off by vacuum distillation. In most instances the distillation residue is analytically pure and requires no further purification measures.
Aliphatic and aromatic hydrocarbons as well as simple and cyclic ethers are suitable as solvents for use in the reaction. It is advantageous to use not only the solvents in pure form, as for example, an aliphatic hydrocarbon compound such as isoctane, but also their mixtures can be used, such as benzine fractions, instance fractions having a boiling range of from to 200 C.
Chlorinated hydrocarbons such as dichlorothane, tetrachlorethylene, and pentachlorethane, can also be used as solvents. Benzene, toluene, o-dichlorbenzene and xylene are examples of suitable aromatic hydrocarbons. Instances of suitable ethers include: diisopropyl ether, diisoamyl ether, diphenyl ether, 1,4-dioxane etc. The above enumeration is indicative of the fact that both aliphatic and aromatic open-chain ethers can be satisfactorily used. Polar solvents such as dimethylsulfoxide, dimethylformamide, the dimethyl ether of diethylene glycol, and decaline, have also been found to be useful as solvents.
The starting materials for use in the process of the invention can be halogenated phenoxy-triazine derivatives containing reactive chlorine atoms, such as have been described in US. Pat. application Ser. No. 737129, now abandoned.
The phosphorus acid esters which can be used in the reaction with the triazine derivatives include the trialkyl phosphites in general. Lower alkyl esters of phosphorus acid, such as triethyl phosphite, tripropyl phosphite, etc., are preferred for the reaction. Halogenated trialkylphosphites, such as tris-(B- chlorethyl)-phosphite can also be advantageously used in the reaction according to the invention.
The saponification of these phosphonic acid ester derivatives with alkali to thereby form the alkali salts of phosphonic acid increases the solubility of the resulting compounds in water.
The saponification to form the salts is carried out by conventional methods, as for instance, by dissolving the phosphonic acid ester derivatives in organic solvents and heating them with an alkali.
The organic solvents which can be used for dissolv- 5 ing the phosphonic acid ester derivatives include alcohols and ketones, as for example ethanol, acetone etc., as well as the solvents mentioned heretofore in connection with the reaction of the halogenphenoxy-striazines with alkyl phosphites.
The preparation of the compounds of the invention in which R represents an amino radical, is carried out by reacting a C-chloride of a halogenated phenoxy-striazine, in the presence of a tertiary amine or of an acid amide as catalyst, at a temperature between 50 C and 250 C and preferably 80 C to 200 C, with an amine of the formula:
HWN
wherein R and R have the same significances as given above. The reaction can be conducted either with the reactants in the fused state or in an inert solvent. The inert solvent then having the function both of a genuine solvent and of a dispersing agent. The solvents which have been enumerated as suitable for use in the reaction of the halogenphenoxy-s-triazine with phosphorus acid esters can also be used for the reaction with the amine Ra H--N/ .34.
The catalysts for use in the reaction are tertiary amines having aliphatic, cycloaliphatic and aromatic radicals in which case the substituted imines are to be understood as constituting a type of cyclic tertiary amine.
Other catalysts which may be used are acid amides or N-mono or disubstituted acid amides of monobasic, aliphatic, aromatic or araliphatic carboxylic acids having one to 18 carbon atoms. These acid amides have been described for instance in US. Pat. application Ser. No. 737,129, now abandoned.
To some extent, however, the amines used for the reaction themselves serve as reaction catalysts, so that the use of a special catalyst of the kind described above can in many instances be dispensed with.
The new compounds and their salts can be used as water repellants, parting agents, dressings for glass fabrics, textile adjuvants, for the surface treatment of various materials and articles because of their fire-retardant, fungicidal, phytotoxic, bactericidal and insecticidal properties. They can also be used as additives for varnishes and enamels.
The following Examples are given for the purpose of more clearly illustrating the invention and are not to be construed as limiting.
EXAMPLE 1 2phosphonic acid diethy1ester,6-di-(trichlorophenoxy)-triazine 50.7 g of 2-chloro-4,6-di-(trichlorophenoxy)-striazine and 18.6 ml of triethylphosphite were weighed out and placed in a 250 ml 4-necked flask equipped with a stirrer, condenser, thermometer and a nitrogen gas introducing tube. The reaction mixture was slowly heated to 155 C and stirred for 2 hours at this temperature while being maintained under a current of nitrogen. The mixture was thereafter cooled to 120 C and the excess triethylphosphite removed by distillation in vacuo. The recovered product had a melting point of 74-78 C.
EXAMPLE 2 diethylester-4,6-di-( pen- Analysis Found Calculated C 31.67 30.60 H 1.51 1.34 N 5.83 5.63 CI 47.10 47.55 F 4.30 4.16
The sodium salt of this compound was prepared as follows: 8 grams of the substance were dissolved in ml of acetone and then added under stirring to a sodium hydroxide solution in water (lgram/S ml H O). After 30 minutes stirring, the solution mixture was evaporated.
EXAMPLE 3 2-[phosphonic acid di-(B-chlorethyD-ester]-4,6-di- (tetrachlorophenoxy)-triazine There were introduced into a 100 ml 4-neck flask provided with stirrer, condenser, thermometer, and nitrogen gas introduction tube, 28.8 g of 2-ch1oro-4,6- di-(tetrachloro-phenoxy)-s-triazine and 13.5 g of tris- B-chlorethylphosphite. While maintained under a current of nitrogen gas, the reaction mixture was slowly heated to 200 C and stirred at this temperature for 2 hours. The recovered product had a melting point of l l l-1 14 C.
Analysis Found Calculated C 3 1 .40 3 1 .20 1-1 1 .35 1 .37 N 5.63 5.67 CI 48.46 48.60 P 4.40 4.20
EXAMPLE 4 2-anilide,4,6di(2,4,6-trichlorophenoxy)-s-triazine 18.4 g of cyanuric chloride, 39.5 g of 2,4,6- trichlorophenol and 0.5 m1 of dimethylcyclohexylamine were introduced into a three-necked flask provided with stirrer, condenser and introduction tube and ml of xylene then added. The mixture was stirred at the boiling temperature of the xylene, and the HCl gas which evolved was flushed out of the reaction mixture with nitrogen gas and trapped in caustic soda solution. After approximately 66% HO had been split off, 9.3 g of aniline were added to the reaction mixture. The reaction was completed after a period of about 29 hours. The precipitate which developed was filtered and dried. The melting point of the product was 186-l88 C.
EXAMPLE 5 2-anilide, 4,6-di-(pentachlorophenoxy)-s-triazine A product having a melting point of 207-209 C was obtained.
In a three-necked flask provided with stirrer, con- EXAMPLE9 denser and introduction tube, 18.4 g of cyanuric 5 chloride, 53.3 g of pentachlorophenol and 0.5 ml of 2'd1'(g'eihylhexyhmmo)'46'dl'(pentachlorophenoxy)-s-tr1az1ne qulnohne were comblned 1n 120 ml of xylene. The rrux- Th d f E l d d ture was stirred at the boilin tem erature of thex lene e proce ure xam? e were repeate an d h HC] h d p fl h d y 19.34 g of 2-chloro-4,6-d1-(pentachlorophenoxy)-san e gas evo ve was e out of the triazine were reacted with 7.18 g of di-(2-ethylhexreaction mixture wlth N and entrapped in NaOI-I solu- 10 ylamine) and Xylene as solvem tiOn. After had been Off, g Of aniline A product was btained having a point of were added to the mixture. Following a period of about 107 11() C, 19 hours, the reaction was completed. The precipitate which was developed was filtered off and dried. M.P. EXAMPLE 10 271-273c.
2-octyl1m1no-4,6-d1-(2,4,6-tr1bromophenoxy)-s- EXAMPLE 6 triazine Using a procedure analogous to that set out in Exam- 2-an1l1de, 4,6-d1-(tr1bromophenoxy)-s-tr1az1ne ple 6, 2225 g of 2 chloro 4,6 di (2,4,6 In a three-necked flask prov1ded=w1th stirrer, con- 20 tribromophenoxy) s triazine were reacted with 338 g denser and introductlon tube, 18.4 g of cyanuric f t i ascatalyst and Xylene assolvent, chloride, g Of tribromophenol and ml Of qum- A prgduct having a melting point of 124 128 C was oline were combined and then 120 ml of xylene were bt i d, added thereto. The mixture was stirred at the boiling In like manner, the compounds listed in the Table temperature of the xylene and the HCl gas which was which follows were prepared.
Elemental analysis Theory Found Plwuoxy-S-triazine Ep., Yiold, rh-rivatives E R2 0. percent C H N 01 131" C H N Cl Br 2-octylirhino-4,6-di-(2,4,6-tribron1o H Octyl 124-128 96 31.0 2. 54 6.46 55.4 31.32 2.98 6. 51 54.510
phvnoxy)-striazi11o. 2-(li-(2-0thylhnxylimino)-4,6-di- 2-ethyl- 2'ethyl- 02-05 05 38.08 3.70 5.73 40.15 38.87 3. 08 5.70 40.17
trihron1opl1enoxyl-striazi 110. hexyl hexyl. 2-5111 lhex 11min5-1,0-d1- 2,4,8- H ..d0 190192 02 31.0 2.43 0. 47 55.5 32.48 2. 6.86 55.02
Lribromophenoxy)-s-triazinc. 2-butylimi110-4.fi-di-(2,4,6-t1ib1'omo- H Butyl 207-209 90 28.15 1.73 6.92 50. 25 28.35 1.54 7.22 58.80
phunoxy)striazine. Z-hntylimi110-4,G-di-(pontachloro- H do 247-250 00 33.5 1.47 8.23 52.1 33.05 1.51 8. 00 51.41
phonoxy)-s-t1iazi110. Z-uthylhvxylimino-4,6-di-(pentachloro- H 2-etl1yl- 189-190 99 37.4 2. 44 7.6 48.2 37.91 2. 43 8.22 48.12
plu-noxy)-s-triazinc. hexyl. 2551 7111111liq-4,04114 501055111010 11 P 050 71...- 185-187 05 37.4 2.44 7.6 48.2 37. 87 2.21 8.44 48.5
pllmmxy)-s-triazi110. 2-(11-12+1.hylhvxyliuiino-4fi-di- 20tl1yl- 2-etl1yl- 107-110 05 43.0 3.78 6.6 41.05 44.77 3. 01 7.05 41.03
p0|11110111orophunoxy)-s-tria7in0. hoxyl hexyl.
evolved was flushed out of the reaction mixture with N 1 claim: and trapped in NaOH solution. After 66 percent of HCl 1. A member of the group consisting of compounds had split off, 9.3 g of aniline were added to the reaction 45 having the formula:
mixture. The reaction had ended after about 19 hours. The precipitate which had developed was filtered off and dried. The melting point of the recovered triazine was 220-222 C.
EXAMPLE 7 EXAMPLE 8 2-butylimino-4,6-di-(2,4,6-tribromophenoxy)-striazine By a procedure analogous to that of Example 4, 22.25 g of 2-chloro-4,6-di-(2,4,6-tribromophenoxy)-striazine were reacted with 2.2 g of n-butylamine and xylene as solvent.
wherein X represents from one to five chlorine atoms, and R represents a member selected from the group of wherein R represents a member of the group consisting of alkyl having one to five carbon atoms,- halogenated alkyl having one to five carbon atoms, alkali metal and ammonium, R is hydrogen or a two to 18 carbon atom member selected from the group consisting of alkyl, cycloalkyl and haloalkyl, and R is a two to 18 carbon atom member selected from the group consisting of alkyl, cycloalkyl, haloalkyl and carbocyclic aryl, wherein R and R taken together are alkylene and taken together with the nitrogen atom to which they are attached can also form a cycloalkylimino ring having no more than six carbon atoms,
6. A compound according to claim 1 designated 2- I anilide, 4,6-di-(pentachlorophenoxy)-s-triazine.
"7. A compound according to claim 1 designated 2- anilide, 4,6-di-(tribromophenoxy )-s-triazine.
8. A compound according to claim 1 designated 2- (2-ethylhexylimino)-4,6-di-(2,3,4,6- tetrachlorophenoxy)-s-triazine.
9. A compound according to claim 1 designated 2- butylimino-4,6-di-(2,4,6-tribromophenoxy)-s-triazine.
10. A compound according to claim 1 designated 2- di-( 2-ethylhexylimino)-4,6-di-(pentachlorophenoxy)- s-triazine.
Claims (9)
- 2. A compound according to claim 1 designated 2-phosphonic acid diethylester-4,6-di-(trichlorophenoxy)-triazine.
- 3. A compound according to claim 1 designated 2-(phosphonic acid di-( Beta -chlorethyl)-ester)-4,6-di-(tetrachlorophenoxy)-triazine.
- 4. A compound according to claim 1 designated 2-phosphonic acid diethylester-4,6-di-(pentachlorophenoxy)-s-triazine.
- 5. A compound according to claim 1 designated 2-anilide, 4,6-di(2,4,6-trichlorophenoxy)-s-triazine.
- 6. A compound according to claim 1 designated 2-anilide, 4,6-di-(pentachlorophenoxy)-s-triazine.
- 7. A compound according to claim 1 designated 2-anilide, 4,6-di-(tribromophenoxy)-s-triazine.
- 8. A compound according to claim 1 designated 2-(2-ethylhexylimino)-4,6-di-(2,3,4,6-tetrachlorophenoxy)-s-triazine.
- 9. A compound according to claim 1 designated 2-butylimino-4,6-di-(2,4,6-tribromophenoxy)-s-triazine.
- 10. A compound according to claim 1 designated 2-di-(2-ethylhexylimino)-4,6-di-(pentachlorophenoxy)-s-triazine.
Applications Claiming Priority (2)
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DE19681770549 DE1770549A1 (en) | 1967-06-15 | 1968-05-31 | Process for the preparation of halophenoxy-s-triazines containing amino groups |
DE19681770591 DE1770591A1 (en) | 1968-06-07 | 1968-06-07 | Linear, segmented polyurethane elastomers |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4104250A (en) * | 1976-08-11 | 1978-08-01 | Borg-Warner Corporation | Flame-retardant polymers with 1,3,5-triazines having halo- and halo-aryl substitutents |
US5230964A (en) * | 1989-10-05 | 1993-07-27 | The Dow Chemical Company | Magnetic recording media a comprising magnetic particles binder and (fluorinated phenoxy)(3-perfluoroalkylphenoxy)-cyclic phosphazene lubricant |
US5656701A (en) * | 1992-11-06 | 1997-08-12 | Sakata Inx Corp. | Polyurethane resins, process for producing the same, and uses thereof |
US20050085584A1 (en) * | 2003-09-18 | 2005-04-21 | Rudiger Musch | Aqueous adhesive dispersions |
US20050234190A1 (en) * | 2004-04-08 | 2005-10-20 | Rolf Gertzmann | Process for the continuous production of an aqueous polyurethane dispersion |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2537816A (en) * | 1951-01-09 | Method-of preparing tjnsaturated | ||
US3165513A (en) * | 1961-12-26 | 1965-01-12 | Dal Mon Research Co | Triazine phosphonium derivatives |
-
1969
- 1969-02-19 US US800699A patent/US3687952A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2537816A (en) * | 1951-01-09 | Method-of preparing tjnsaturated | ||
US3165513A (en) * | 1961-12-26 | 1965-01-12 | Dal Mon Research Co | Triazine phosphonium derivatives |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4104250A (en) * | 1976-08-11 | 1978-08-01 | Borg-Warner Corporation | Flame-retardant polymers with 1,3,5-triazines having halo- and halo-aryl substitutents |
US5230964A (en) * | 1989-10-05 | 1993-07-27 | The Dow Chemical Company | Magnetic recording media a comprising magnetic particles binder and (fluorinated phenoxy)(3-perfluoroalkylphenoxy)-cyclic phosphazene lubricant |
US5656701A (en) * | 1992-11-06 | 1997-08-12 | Sakata Inx Corp. | Polyurethane resins, process for producing the same, and uses thereof |
US20050085584A1 (en) * | 2003-09-18 | 2005-04-21 | Rudiger Musch | Aqueous adhesive dispersions |
US20050234190A1 (en) * | 2004-04-08 | 2005-10-20 | Rolf Gertzmann | Process for the continuous production of an aqueous polyurethane dispersion |
US7345110B2 (en) | 2004-04-08 | 2008-03-18 | Bayer Materialscience Ag | Process for the continuous production of an aqueous polyurethane dispersion |
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