ES372712A1 - Quaternary ammonium salts as stabilizers for emulsion polymerisation - Google Patents
Quaternary ammonium salts as stabilizers for emulsion polymerisationInfo
- Publication number
- ES372712A1 ES372712A1 ES372712A ES372712A ES372712A1 ES 372712 A1 ES372712 A1 ES 372712A1 ES 372712 A ES372712 A ES 372712A ES 372712 A ES372712 A ES 372712A ES 372712 A1 ES372712 A1 ES 372712A1
- Authority
- ES
- Spain
- Prior art keywords
- allyl
- ammonium
- dimethyl ammonium
- sodium
- quaternary ammonium
- 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
- 239000000839 emulsion Substances 0.000 title abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 title abstract 2
- 239000003381 stabilizer Substances 0.000 title abstract 2
- -1 quaternary ammonium halide Chemical class 0.000 abstract 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- MHGOKSLTIUHUBF-UHFFFAOYSA-M 2-ethylhexyl sulfate(1-) Chemical compound CCCCC(CC)COS([O-])(=O)=O MHGOKSLTIUHUBF-UHFFFAOYSA-M 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 abstract 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000004141 Sodium laurylsulphate Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 abstract 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract 1
- AXIPBRXJGSXLHF-UHFFFAOYSA-N piperidine;pyrrolidine Chemical compound C1CCNC1.C1CCNCC1 AXIPBRXJGSXLHF-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- BDRVEARQBLPFIP-UHFFFAOYSA-M triethyl(prop-2-enyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC=C BDRVEARQBLPFIP-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
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)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
Quaternary ammonium salts of the general formula (where V is a 4-hydroxy-maleoyloxy, 4-hydroxycitraconoyloxy, vinyl or isopropenyl group A is alkylene containing from 1-3 carbon atoms, being methylene when V is vinyl or isopropenyl R 1 -R 3 are independent univalent organic radicals each containing less than 8 carbon atoms or R 1 is as defined and R 2 and R 3 together with the linking nitrogen atom constitute a pyrrolidinium piperidinium, morpholinium, or a tetrahydro-S-triazinium-2-one radical or R 1 -R 3 together with the linking nitrogen atom constitute a pyridinium or substituted pyridinium group Y- is a sulphonate, sulphate, sulphite or phosphate group and R 4 is a lipophilic radical containing at least one hydrocarbon chain of 8-28 carbon atoms) may be prepared by forming a quaternary ammonium halide of formula V.A.N+R 1 R 2 R 3 Cl- (or Br-) and reacting this compound with a lipophilic salt R 4 YX (X being an alkali metal or ammonium group). Specified lipophilic salts include sodium lauryl sulphate, di-tridecyl sodium sulphosuccinate, di-octyl sodium sulphosuccinate, sodium 2-ethyl hexyl sulphate, sodium dodecyl phenyl sulphonate, sodium di-2- ethylhexyl phosphate, and ammonium salts of sulphated alkyl phenoxy polyethyleneoxy ethanols. The quaternary ammonium halides are prepared by reaction of (a) an appropriate unsaturated alkylene halide with a tertiary amine (b) a halogenated compound with an unsaturated amine or (c) in two steps by condensation of maleic or citraconic anhydride with an amino alcohol followed by quaternization of the resulting half ester, e.g. by reaction with chloroacetonitrile, a halomethyl alkyl ether, a haloester or a haloacetamide. Examples detail the preparation of the following chlorides :-4-hydroxy maleoyloxy 2-acetamido dimethyl ammonium, allyl pyridinium, allyl n - butoxymethyl dimethyl ammonium, allyl methyl morpholinium, 4 - hydroxycitraconyloxyethyl 2-acetamido dimethyl ammonium, allyl benzyl dimethyl ammonium, allyl 2-acetamido dimethyl ammonium, 4-hydroxy maleoyloxy isopropyl 2-acetamido dimethyl ammonium, and also allyl triethyl ammonium bromide. The compounds are monomeric emulsion stabilizers (see Division C3).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76935568A | 1968-10-21 | 1968-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES372712A1 true ES372712A1 (en) | 1972-02-16 |
Family
ID=25085201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES372712A Expired ES372712A1 (en) | 1968-10-21 | 1969-10-20 | Quaternary ammonium salts as stabilizers for emulsion polymerisation |
Country Status (13)
| Country | Link |
|---|---|
| BE (1) | BE740585A (en) |
| BR (1) | BR6913505D0 (en) |
| CA (1) | CA939668A (en) |
| CH (1) | CH525253A (en) |
| DE (1) | DE1952356C3 (en) |
| DK (1) | DK130006B (en) |
| ES (1) | ES372712A1 (en) |
| FI (1) | FI50533C (en) |
| FR (1) | FR2021141A1 (en) |
| GB (1) | GB1240571A (en) |
| NL (1) | NL158808B (en) |
| NO (1) | NO136152C (en) |
| SE (1) | SE384498B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1298099A (en) * | 1969-10-20 | 1972-11-29 | Kendall & Co | Unsaturated quaternary ammonium compounds and copolymers containing them |
| JPS4948611A (en) * | 1972-09-14 | 1974-05-11 | ||
| DE4216314A1 (en) * | 1992-05-16 | 1993-11-18 | Basf Ag | Process for the preparation of N-allyl compounds |
-
1969
- 1969-04-30 CA CA050,213A patent/CA939668A/en not_active Expired
- 1969-10-02 GB GB4855969A patent/GB1240571A/en not_active Expired
- 1969-10-16 FI FI298369A patent/FI50533C/en active
- 1969-10-17 DE DE19691952356 patent/DE1952356C3/en not_active Expired
- 1969-10-20 FR FR6935832A patent/FR2021141A1/fr active Pending
- 1969-10-20 CH CH1567469A patent/CH525253A/en not_active IP Right Cessation
- 1969-10-20 NO NO415669A patent/NO136152C/en unknown
- 1969-10-20 ES ES372712A patent/ES372712A1/en not_active Expired
- 1969-10-20 SE SE1434969A patent/SE384498B/en unknown
- 1969-10-21 DK DK556569A patent/DK130006B/en not_active IP Right Cessation
- 1969-10-21 NL NL6915891A patent/NL158808B/en not_active IP Right Cessation
- 1969-10-21 BE BE740585D patent/BE740585A/xx not_active IP Right Cessation
- 1969-10-21 BR BR21350569A patent/BR6913505D0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1240571A (en) | 1971-07-28 |
| NL6915891A (en) | 1970-04-23 |
| CH525253A (en) | 1972-07-15 |
| DK130006B (en) | 1974-12-09 |
| DK130006C (en) | 1975-05-12 |
| FR2021141A1 (en) | 1970-07-17 |
| DE1952356A1 (en) | 1970-04-23 |
| DE1952356B2 (en) | 1979-06-13 |
| FI50533C (en) | 1976-04-12 |
| BE740585A (en) | 1970-04-01 |
| NL158808B (en) | 1978-12-15 |
| NO136152C (en) | 1977-07-27 |
| NO136152B (en) | 1977-04-18 |
| DE1952356C3 (en) | 1980-02-14 |
| CA939668A (en) | 1974-01-08 |
| BR6913505D0 (en) | 1973-05-03 |
| SE384498B (en) | 1976-05-10 |
| FI50533B (en) | 1975-12-31 |
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