GB471048A - Improvements in the manufacture and production of nitrogenous condensation products of high molecular weight - Google Patents
Improvements in the manufacture and production of nitrogenous condensation products of high molecular weightInfo
- Publication number
- GB471048A GB471048A GB3556935A GB3556935A GB471048A GB 471048 A GB471048 A GB 471048A GB 3556935 A GB3556935 A GB 3556935A GB 3556935 A GB3556935 A GB 3556935A GB 471048 A GB471048 A GB 471048A
- Authority
- GB
- United Kingdom
- Prior art keywords
- halogen
- amines
- abietinyl
- halogenated
- reacting
- 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
- 239000007859 condensation product Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 12
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 12
- 150000001412 amines Chemical class 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 6
- 239000000047 product Substances 0.000 abstract 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 6
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 abstract 6
- 150000001298 alcohols Chemical class 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- -1 halogen alkylamines Chemical class 0.000 abstract 5
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 abstract 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- 150000001805 chlorine compounds Chemical class 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 4
- 239000011347 resin Substances 0.000 abstract 4
- 229920005989 resin Polymers 0.000 abstract 4
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 abstract 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 3
- 108010077895 Sarcosine Proteins 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- 150000001413 amino acids Chemical class 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 229920000768 polyamine Polymers 0.000 abstract 3
- 229940043230 sarcosine Drugs 0.000 abstract 3
- JTAXUBKTCAOMTN-UHFFFAOYSA-N Abietinol Natural products CC(C)C1=CC2C=CC3C(C)(CO)CCCC3(C)C2CC1 JTAXUBKTCAOMTN-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- GQRUHVMVWNKUFW-LWYYNNOASA-N abieta-7,13-dien-18-ol Chemical compound OC[C@]1(C)CCC[C@]2(C)[C@@H](CCC(C(C)C)=C3)C3=CC[C@H]21 GQRUHVMVWNKUFW-LWYYNNOASA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract 2
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 abstract 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 abstract 1
- 229920002955 Art silk Polymers 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 239000000834 fixative Substances 0.000 abstract 1
- 238000005187 foaming Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000009877 rendering Methods 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 229960003080 taurine Drugs 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Resinous condensation products, useful as textile assistants, of the general formula R--X--R1--N, where R represents the cyclic radicle of abietic acid or its hydrogenation products, R1 an alkylene or hydroxyalkylene radicle, N represents tri- or pentavalent nitrogen and X may comprise the groups --CH2O--, --CH2NY, --CH2NYCO--. --CH2OCO----COO--, or --CONY--, Y being a hydrogen atom or an organic radicle, are obtained by (1) causing abietinyl derivatives containing a reactive halogen atom, such as abietinyl halogen alkyl ethers, amines, esters or amides, to act on amines or nitrogenous heterocyclic bases or their substitution products, or (2) reacting resin alcohols with halogen alkylamines, chlorides of amino acids, alkylolamines or polyamines; reacting resin amines with halogen alkylamines, chlorides of amino acids or alkylolamines; or reacting resin acids with alkylolamines or polyamines. Starting materials for (1) may comprise abietinyl halogen alkyl ethers obtainable by reacting abietinol or tetrahydroabietinol with halogenated alcohols, with ethylene oxide followed by treatment with phosphorus oxychloride, or with halogenated hydroxyethers, e.g. b -chlorb <1>-hydroxy-diethyl ether; abietinyl halogenalkylamines obtainable by treating abietinylamine with alkylene oxide and subsequently replacing the terminal hydroxyl group by halogen, or by condensing abietinylamine with halogenated hydroxy ethers or halogenated alcohols; abietinyl halogen-alkyl esters obtainable by reacting abietic acid with halogenated alcohols, with epichlorhydrin or with alkylene oxides followed by treatment with phosphorus oxychloride, or by reacting abietinol or tetrahydroabietinol with halogenated aliphatic acids; and abietinyl halogen alkyl amides obtainable by condensing resin acids with halogen alkylamines, or by condensing abietinylamines with halogenated aliphatic acids. The abietinyl halogen alkyl derivatives are caused to react at elevated temperature and, if desired, under pressure and/or in the presence of diluents, with amines, e.g. aliphatic, cycloaliphatic, aromatic, aliphatic-aromatic or with nitrogenous heterocyclic bases. Suitable amines and heterocyclic bases are diethylamine, trimethylamine, ethylenediamine, dodecylamine, oleylamine, piperidine, aniline, methylaniline, and pyridine. Substituted amines containing carboxyl, ether, ester or sulphonic groups, e.g. sarcosine and taurine, may be employed. Halogen alkylamides or polyamines, alkylolamines and chlorides of amino acids for method (2) are obtainable by reacting halogenated amines, alcohols and acid chlorides with amines or nitrogenous heterocyclic bases. In examples: (1) dihydroabietinol is heated, under reflux, with monochloracetic acid and the viscous ester is further heated with trimethylamine dissolved in alcohol, yielding a brown crystalline product which, in aqueous solution, has good wetting and foaming power; wax-like products may be obtained by using pyridine, aniline, methylaniline, glycocoll or sarcosine in place of trimethylamine; the sodium salts of the glycocoll and sarcosine products have soap-like properties and may be employed as fixatives for tanning agents and for rendering artificial silk fabrics slip-proof; (2) dihydroabietinylamine is reacted with monochloracetyl chloride and the amide further reacted with trimethylamine or pyridine giving a water-soluble, wax-like product; (3) a chlorinated ether is obtained by treating an industrial mixture of di- and tetrahydroabietinol with epichlorhydrin, or with ethylene oxide followed by phosphorus oxychloride, and is further reacted with trimethylamine or pyridine; (4) colophony or hydrogenated abietic acid is reacted with epichlorhydrin and further reacted with trimethylamine; (5) abietinylamine is slowly introduced into a boiling mixture obtained by running pyridine into a benzene solution of chloracetyl chloride, the benzene is distilled off and the residue heated at 130--150 DEG C. until the reaction product is soluble in water; (6) abietic acid is heated with the reaction product of pyridine and b -chlor-b <1>-hydroxy-diethyl ether. Specification 369,614 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3556935A GB471048A (en) | 1935-12-23 | 1935-12-23 | Improvements in the manufacture and production of nitrogenous condensation products of high molecular weight |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3556935A GB471048A (en) | 1935-12-23 | 1935-12-23 | Improvements in the manufacture and production of nitrogenous condensation products of high molecular weight |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB471048A true GB471048A (en) | 1937-08-23 |
Family
ID=10379184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3556935A Expired GB471048A (en) | 1935-12-23 | 1935-12-23 | Improvements in the manufacture and production of nitrogenous condensation products of high molecular weight |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB471048A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2433449A (en) * | 1937-11-05 | 1947-12-30 | Chem Ind Basel | Condensation products and process of preparing the same |
-
1935
- 1935-12-23 GB GB3556935A patent/GB471048A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2433449A (en) * | 1937-11-05 | 1947-12-30 | Chem Ind Basel | Condensation products and process of preparing the same |
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