GB949848A - Metal chelate containing polymers - Google Patents
Metal chelate containing polymersInfo
- Publication number
- GB949848A GB949848A GB3576660A GB3576660A GB949848A GB 949848 A GB949848 A GB 949848A GB 3576660 A GB3576660 A GB 3576660A GB 3576660 A GB3576660 A GB 3576660A GB 949848 A GB949848 A GB 949848A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- formula
- group
- phenyl
- oximinopropionyl
- 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
- 229910052751 metal Inorganic materials 0.000 title abstract 4
- 239000002184 metal Substances 0.000 title abstract 4
- 229920000642 polymer Polymers 0.000 title abstract 3
- 239000013522 chelant Substances 0.000 title abstract 2
- -1 polymethylene group Polymers 0.000 abstract 8
- 125000005646 oximino group Chemical group 0.000 abstract 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- 235000010290 biphenyl Nutrition 0.000 abstract 2
- 125000006267 biphenyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003822 epoxy resin Substances 0.000 abstract 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 229920000647 polyepoxide Polymers 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 2
- BJESYYVKBBDSMI-UHFFFAOYSA-N 2,5-bis(hydroxyimino)-1,6-diphenylhexane-1,6-dione Chemical compound C(C1=CC=CC=C1)(=O)C(CCC(=NO)C(C1=CC=CC=C1)=O)=NO BJESYYVKBBDSMI-UHFFFAOYSA-N 0.000 abstract 1
- LOLHGPMBGBAZNM-UHFFFAOYSA-N 2-hydroxyimino-1-[4-[4-(2-hydroxyiminopropanoyl)phenoxy]phenyl]propan-1-one Chemical compound N(O)=C(C(=O)C1=CC=C(C=C1)OC1=CC=C(C=C1)C(C(C)=NO)=O)C LOLHGPMBGBAZNM-UHFFFAOYSA-N 0.000 abstract 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 abstract 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 239000004150 EU approved colour Substances 0.000 abstract 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- BTZXROSTAHDTKC-UHFFFAOYSA-N N(O)=C(C(=O)C1=CC=C(C=C1)CC1=CC=C(C=C1)C(C(C)=NO)=O)C Chemical compound N(O)=C(C(=O)C1=CC=C(C=C1)CC1=CC=C(C=C1)C(C(C)=NO)=O)C BTZXROSTAHDTKC-UHFFFAOYSA-N 0.000 abstract 1
- CWSPCMCRHNXIPL-UHFFFAOYSA-N N(O)=C(C(C)=NO)C1=CC=C(C=C1)OC1=CC=C(C=C1)C(C(C)=NO)=NO Chemical compound N(O)=C(C(C)=NO)C1=CC=C(C=C1)OC1=CC=C(C=C1)C(C(C)=NO)=NO CWSPCMCRHNXIPL-UHFFFAOYSA-N 0.000 abstract 1
- AQTYZAKTQXAWGJ-UHFFFAOYSA-N N-[1,2,4-tris(hydroxyimino)-1,6-diphenylhexan-3-ylidene]hydroxylamine Chemical compound C1(=CC=CC=C1)C(C(C(C(CCC1=CC=CC=C1)=NO)=NO)=NO)=NO AQTYZAKTQXAWGJ-UHFFFAOYSA-N 0.000 abstract 1
- QPPJANVBGGFYHU-UHFFFAOYSA-N N-[1-(4-ethylphenyl)-1-hydroxyiminopropan-2-ylidene]hydroxylamine Chemical compound N(O)=C(C(C)=NO)C1=CC=C(C=C1)CC QPPJANVBGGFYHU-UHFFFAOYSA-N 0.000 abstract 1
- KCUQAYSMVAHUBT-UHFFFAOYSA-N N-[1-[4-[[4-[N-hydroxy-C-(N-hydroxy-C-methylcarbonimidoyl)carbonimidoyl]phenyl]methyl]phenyl]-1-hydroxyiminopropan-2-ylidene]hydroxylamine Chemical compound N(O)=C(C(C)=NO)C1=CC=C(C=C1)CC1=CC=C(C=C1)C(C(C)=NO)=NO KCUQAYSMVAHUBT-UHFFFAOYSA-N 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- 239000004157 Nitrosyl chloride Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 abstract 1
- 239000011968 lewis acid catalyst Substances 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 abstract 1
- 235000019392 nitrosyl chloride Nutrition 0.000 abstract 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 abstract 1
- 125000003544 oxime group Chemical group 0.000 abstract 1
- 150000002923 oximes Chemical class 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Bis (a -keto-oximes) or bis (1,2-dioximes) of formula: <FORM:0949848/C2/1> where R is an alkyl group, Z1 and Z2 either both represent an oximino group >NOH or Z1 represent an oximino group and Z2 represents an oxygen atom, and X represents a group of formula: <FORM:0949848/C2/2> where Y is a single bond, an oxygen atom, or a methylene or polymethylene group are made by the following series of reactions:-(1) A compound of formula: <FORM:0949848/C2/3> is reacted with a chloride or an anhydride of an acid of formula: <FORM:0949848/C2/4> in the presence of a Lewis acid catalyst to yield a product of formula: <FORM:0949848/C2/5> (2) This product is nitrosated, e.g. by reaction with (a) an inorganic nitrite and an acid, (b) nitrosyl chloride, (c) an alkyl nitrite in the presence of an alkali metal alkoxide or (d) an alkyl nitrite in the presence of hydrogen chloride; whereby bis (a -keto-oximes) are produced, (3) These bis (a -keto-oximes) are possibly reacted with hydroxylamine hydrochloride to produce bis (1,2-dioximes). In examples, (A) a , b -bis[p-(2-oximinopropionyl) phenyl] ethane is made by reacting 4, 41-dipropionyldibenzyl with n-butyl nitrite in dry chloroform whilst passing hydrogen chloride through the reaction mixture; (B), (C), (D), (E) and (L); bis [p-(2-oximinopropionyl) phenyl] ether, bis [p-(2-oximinopropionyl) phenyl] methane, a , g - bis [p-(2-oximinopropionyl) phenyl] propane p, p1-bis (2-oximinopropionyl) diphenyl and 1, 4-dibenzoyl-1, 4-dioximinobutane are similarly prepared; (F) a , b -bis [p-(1, 2-dioximinopropyl) phenyl] ethane is made by reacting hydroxylamine hydrochloride dissolved in water with the product of Example (A) in methanol; (G), (H), (I), (J) and (K) bis [p-(1,2-dioximinopropyl) phenyl] ether, bis [p-(1,2-dioximinopropyl) phenyl] methane, a , g - bis [p-(1,2-dioximinopropyl) phenyl] propane, p, p1-bis (1,2-dioximinopropyl) diphenyl and 1, 6-diphenyl-tetra-oximinohexane are similarly prepared. The oximes are reacted with metal salts to yield polymeric co-ordination compound (see Division C3).ALSO:The invention comprises polymeric co-ordination compounds containing recurring units of formula: <FORM:0949848/C3/1> or of formula: <FORM:0949848/C3/2> where M represents an atom of a metal which is capable of forming a chelate structure with a ligand containing an oximino group, R is an alkyl group and X is a group of formula: <FORM:0949848/C3/3> where Y represents a single bond or an atom of oxygen or a methylene or polymethylene group. The polymers are made by reacting a salt (e.g. the acetate) of the metal M with a bis-(a -ketooxime) or a bis-(1,2-dioxime) of formula: <FORM:0949848/C3/4> where Z1 and Z2 either both represent the oximino group >NOH or Z1 represents the oximino group and Z2 represents an oxygen atom, and X represents a group of formula III. Suitable metal ions are Ni11, Co11, Fe11, Pb11 and Cu11. The terminal oxime groups of the polymers may be reacted with epichlorhydrin (e.g. in aqueous sodium hydroxide solution) to form epoxy resins. The epoxy resins may be hardened by aliphatic or aromatic primary, secondary or tertiary amines (including Mannich bases), amino-alcohols, guanidine, phenylguanidine, dicyandiamide, aniline-formaldehyde resins, polyaminostyrenes and polyamides derived from polymeric fat acids. The curable composition may also contain a mono- or poly-glycidyl ether of a mono- or poly-hydric alcohol or phenol, a polyglycidyl ester of a polycarboxylic acid, or the dehydrohalogenation product of the reaction product of epichlorhydrin with a primary or secondary amine. Fillers, plasticisers or colouring agents may also be added.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3576660A GB949848A (en) | 1960-10-18 | 1960-10-18 | Metal chelate containing polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3576660A GB949848A (en) | 1960-10-18 | 1960-10-18 | Metal chelate containing polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB949848A true GB949848A (en) | 1964-02-19 |
Family
ID=10381341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3576660A Expired GB949848A (en) | 1960-10-18 | 1960-10-18 | Metal chelate containing polymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB949848A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106290216A (en) * | 2016-09-21 | 2017-01-04 | 天津科技大学 | The detection method of ethylene oxidic ester in a kind of oils and fats |
-
1960
- 1960-10-18 GB GB3576660A patent/GB949848A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106290216A (en) * | 2016-09-21 | 2017-01-04 | 天津科技大学 | The detection method of ethylene oxidic ester in a kind of oils and fats |
| CN106290216B (en) * | 2016-09-21 | 2018-12-18 | 天津科技大学 | The detection method of ethylene oxidic ester in a kind of grease |
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