New! View global litigation for patent families

US3687952A - HALOGENPHENOXY-s-TRIAZINE DERIVATIVES HAVING IMPROVED SOLUBILITY - Google Patents

HALOGENPHENOXY-s-TRIAZINE DERIVATIVES HAVING IMPROVED SOLUBILITY Download PDF

Info

Publication number
US3687952A
US3687952A US3687952DA US3687952A US 3687952 A US3687952 A US 3687952A US 3687952D A US3687952D A US 3687952DA US 3687952 A US3687952 A US 3687952A
Authority
US
Grant status
Grant
Patent type
Prior art keywords
triazine
di
alkyl
reaction
atoms
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 - Lifetime
Application number
Inventor
Roshdy Ismail
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dynamit Nobel AG
Original Assignee
Dynamit Nobel AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Grant date

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6515Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6521Six-membered rings
    • C07F9/65213Six-membered rings the phosphorus atom is bonded to a cyclic carbon atom, directly or through a heteroatom other than nitrogen, e.g. or
    • C07F9/65216Six-membered rings the phosphorus atom is bonded to a cyclic carbon atom, directly or through a heteroatom other than nitrogen, e.g. or directly bonded
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12Prepolymer 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

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.

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)

  1. 2. A compound according to claim 1 designated 2-phosphonic acid diethylester-4,6-di-(trichlorophenoxy)-triazine.
  2. 3. A compound according to claim 1 designated 2-(phosphonic acid di-( Beta -chlorethyl)-ester)-4,6-di-(tetrachlorophenoxy)-triazine.
  3. 4. A compound according to claim 1 designated 2-phosphonic acid diethylester-4,6-di-(pentachlorophenoxy)-s-triazine.
  4. 5. A compound according to claim 1 designated 2-anilide, 4,6-di(2,4,6-trichlorophenoxy)-s-triazine.
  5. 6. A compound according to claim 1 designated 2-anilide, 4,6-di-(pentachlorophenoxy)-s-triazine.
  6. 7. A compound according to claim 1 designated 2-anilide, 4,6-di-(tribromophenoxy)-s-triazine.
  7. 8. A compound according to claim 1 designated 2-(2-ethylhexylimino)-4,6-di-(2,3,4,6-tetrachlorophenoxy)-s-triazine.
  8. 9. A compound according to claim 1 designated 2-butylimino-4,6-di-(2,4,6-tribromophenoxy)-s-triazine.
  9. 10. A compound according to claim 1 designated 2-di-(2-ethylhexylimino)-4,6-di-(pentachlorophenoxy)-s-triazine.
US3687952A 1967-06-15 1969-02-19 HALOGENPHENOXY-s-TRIAZINE DERIVATIVES HAVING IMPROVED SOLUBILITY Expired - Lifetime US3687952A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19681770549 DE1770549A1 (en) 1967-06-15 1968-05-31 A process for the preparation of amino-containing halophenoxy-s-triazines
DE19681770591 DE1770591A1 (en) 1968-06-07 1968-06-07 Linear, segmented polyurethane elastomers

Publications (1)

Publication Number Publication Date
US3687952A true US3687952A (en) 1972-08-29

Family

ID=25755564

Family Applications (1)

Application Number Title Priority Date Filing Date
US3687952A Expired - Lifetime US3687952A (en) 1967-06-15 1969-02-19 HALOGENPHENOXY-s-TRIAZINE DERIVATIVES HAVING IMPROVED SOLUBILITY

Country Status (1)

Country Link
US (1) US3687952A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
US3711389A (en) Process for treating polymeric substrates with high-energy radiation
US2948718A (en) New n-heterocyclic compounds
US2599807A (en) Alkylene polyamine methylene phosphonic acids
US4440921A (en) Coupling of polyorganophosphazenes to carboxylic acid
US2758115A (en) Derivatives of thiophosphoric acid
US3927080A (en) Process for producing N-phosphonomethyl glycine
US4327039A (en) Process for the production of 3-amino-1-hydroxypropane-1,1-diphosphonic acid
US3984448A (en) Production of dialkylthiophosphates
US4574154A (en) Triazine addition compounds
US2985685A (en) Alkanolamine aluminates as catalysts for ester redistribution
US4386079A (en) Method of treating depression
US2761874A (en) Amino derivatives of n-alkyl substituted aspartic acids and their functional derivatives
US2328358A (en) Organic compound and process for preparing the same
US4020091A (en) Chelation
US2574516A (en) Unsaturated aliphatic phosphonamides
US4154930A (en) Pentate salts of amino-s-triazines
US2685581A (en) Organic phosphorus compounds
Ulrich et al. The Reaction of 1, 3-Disubstituted Ureas with Phosphorus Pentachloride1
US3244713A (en) Novel hydroxyalkyl substituted s-triazines
US2731487A (en) Asymmetric tertiary alkyl trithiocarbonates
US2848475A (en) Substituted methylene bis
Schroeder et al. Some Reactions of Cyameluric Chloride
US2832750A (en) Organo tin compounds, method of making same, and mixtures thereof with halogen-containing resins
EP0649841A1 (en) Process for the preparation of hydroxyphenyl-substituted 1,3,5-triazines
US3075979A (en) Preparation of trialkyl isocyanusates