GB1077997A - A process for the preparation of sulphur-containing derivatives of polymerization products of tetrahydrofuran - Google Patents
A process for the preparation of sulphur-containing derivatives of polymerization products of tetrahydrofuranInfo
- Publication number
- GB1077997A GB1077997A GB22364/64A GB2236464A GB1077997A GB 1077997 A GB1077997 A GB 1077997A GB 22364/64 A GB22364/64 A GB 22364/64A GB 2236464 A GB2236464 A GB 2236464A GB 1077997 A GB1077997 A GB 1077997A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- tetrahydrofuran
- organic
- acid
- metal sulphide
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 title abstract 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 title abstract 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract 3
- 239000005864 Sulphur Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 238000006116 polymerization reaction Methods 0.000 title 1
- -1 tetrahydrofuran compound Chemical class 0.000 abstract 12
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 4
- 150000001340 alkali metals Chemical class 0.000 abstract 4
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 4
- 150000001450 anions Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- UODGHRYECKYJEB-UHFFFAOYSA-N 1-aminobutane-1-thiol Chemical class CCCC(N)S UODGHRYECKYJEB-UHFFFAOYSA-N 0.000 abstract 2
- DJZAFAJXGDOEMY-UHFFFAOYSA-N 1-aminopentane-1-thiol Chemical class CCCCC(N)S DJZAFAJXGDOEMY-UHFFFAOYSA-N 0.000 abstract 2
- NZSNWIOVGALACV-UHFFFAOYSA-N 2-(methylamino)ethanethiol Chemical compound CNCCS NZSNWIOVGALACV-UHFFFAOYSA-N 0.000 abstract 2
- CFPHMAVQAJGVPV-UHFFFAOYSA-N 2-sulfanylbutanoic acid Chemical class CCC(S)C(O)=O CFPHMAVQAJGVPV-UHFFFAOYSA-N 0.000 abstract 2
- JSGPBRQYMLFVJQ-UHFFFAOYSA-N 2-sulfanylhexanoic acid Chemical class CCCCC(S)C(O)=O JSGPBRQYMLFVJQ-UHFFFAOYSA-N 0.000 abstract 2
- IMGGANUNCHXAQF-UHFFFAOYSA-N 2-sulfanylpentanoic acid Chemical class CCCC(S)C(O)=O IMGGANUNCHXAQF-UHFFFAOYSA-N 0.000 abstract 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 abstract 2
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical class OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 abstract 2
- 229910001216 Li2S Inorganic materials 0.000 abstract 2
- 239000003513 alkali Substances 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001805 chlorine compounds Chemical class 0.000 abstract 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 abstract 2
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 abstract 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229960003151 mercaptamine Drugs 0.000 abstract 2
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 239000002685 polymerization catalyst Substances 0.000 abstract 2
- 230000000379 polymerizing effect Effects 0.000 abstract 2
- 229910052979 sodium sulfide Inorganic materials 0.000 abstract 2
- 229940035024 thioglycerol Drugs 0.000 abstract 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 abstract 2
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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
- C08G65/3348—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing nitrogen in addition to sulfur
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
- C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Sulphur-containing tetrahydrofuran polymers are obtained by reacting at least one tetrahydrofuran compound of the formula Cl-[(CH2)4-O]m-Z wherein m is 2-70 when Z is hydrogen, an organic acyl radical, or an "inorganic oxyacid anion" (see below), or m is 1-70 when Z is [-(CH2)4-Cl], with an alkali metal sulphide or an alkaline earth metal sulphide or with an organic mercapto compound, and, if desired, further reacting the product with an alkali metal sulphide or an alkaline earth metal sulphide or with an organic mercapto compound. The tetrahydrofuran compounds (I) are obtained by polymerizing tetrahydrofuran using acid chlorides as polymerization catalyst. They may have a M.W. of 500-2000 and may be (a) Cl-[(CH2)4-O]m1-Q (II) where Q is an organic acyl radical or an "inorganic oxyacid anion" (i.e. a radical obtained by the removal of an OH group from an inorganic oxyacid) and m1 is 2-70; or (b) the corresponding hydrolysed product:-Cl-[(CH2)4-O]m1-H (III) or (c) derivatives of the formula <FORM:1077997/C3/1> wherein m11 is 1-70. If compounds (II), (III) or (IV) are reacted with an organic mercapto compound which contains a reactive group, then products containing terminal active groups are obtained. Suitable alkali metal- or alkaline-earth metal sulphides are Na2S, K2S, CaS, BaS, Li2S and MgS. Suitable organic mercapto compounds which may contain reactive-OH, -NH2, or -COOH groups are mercaptoethanol, thioglycollic acid, thioethanolamine, hydroxy-propylmercaptans, thioglycerol, thiolactic acid, thiohydracrylic acid, methylaminoethyl - mercaptan, butanolthiols, mercaptobutyric acids, aminobutane - thiols, aminopentanethiols, mercaptovaleric acids, mercaptocaproic acids and thiophenol derivatives. Specified products which may be obtained by this process are compounds of the formula <FORM:1077997/C3/2> wherein X represents OH, -S(CH2)qOH, -S(CH2)qNH2 or -S(CH2)rCOOH and Y represents a -(CH2)-qOH, -(CH2)qNH2, -(CH2)rCOOH or -[(CH2)4-O]m1-H, n is 1-70, m1 is 2-70, p is 1-10, q is 2-6 and r is 1-5, and wherein X cannot be basic when Y is acid and vice versa. Examples are given for the production of compounds (V).ALSO:Sulphur-containing tetrahydrofuran polymers are obtained by reacting at least one tetrahydrofuran compound of the formula Cl-[(CH2)4-O]m-Z (I) wherein m is 2-70 when Z is hydrogen, an organic acyl radical, or an "inorganic oxyacid anion" (see below), or m is 1-70 when Z is [-(CH2)4-Cl], with an alkali metal sulphide or an alkaline earth metal sulphide or with an organic mercapto compound, and, if desired, further reacting the product with an alkali metal sulphide or an alkaline earth metal sulphide or with an organic mercapto compound. The tetrahydrofuran compounds (I) are obtained by polymerizing tetrahydrofuran using acid chlorides as polymerization catalyst. They may have a M.W. of 500-2000 and may be (a) Cl-[(CH2)4-O]m1-Q (II) where Q is an organic acyl radical or an "in-organic oxyacid anion" (i.e. a radical obtained by the removal of an OH group from an inorganic oxyacid) and m1 is 2-70; or (b) the corresponding hydrolysed product Cl-[(CH2)4-O]m1H (III) or (c) derivatives of the formula Cl[(CH2)4-O]m11-(CH2)4-Cl (IV) wherein m11 is 1-70. If compounds (II), (III) or (IV) are reacted with an organic mercapto compound which contains a reactive group, then products containing terminal active groups are obtained. Suitable alkali metal- or alkaline earth metals sulphides are Na2S, K2S, CaS, BaS, Li2S and MgS. Suitable organic mercapto compounds which may contain reactive -OH, -NH2, or -COOH groups are mercaptoethanol, thioglycollic acid, thioethanolamine, hydroxy-propylmercaptans, thioglycerol, thiolactic acid, thiohydracrylic acid, methylaminoethyl - mercaptan, butanolthiols, mercaptobutyric acids, aminobutane-thiols, aminopentanethiols, mercaptovaleric acids, mercaptocaproic acids and thiophenol derivatives. Specified products which may be obtaine by this process are compounds of the formula <FORM:1077997/C2/1> wherein X represents OH, -S(CH2)qOH, -S(CH2)qNH2 or -S(CH2)rCOOH and Y represents a -(CH2)-qOH, -(CH2)qNH2, -(CH2)rCOOH or -[(CH2)4-O]m1-H, n is 1-70, m1 is 2-70, p is 1-10, q is 2-6 and r is 1-5, and wherein X cannot be basic when Y is acid and vice versa. Examples are given for the production of compounds (V).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0039889 | 1963-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1077997A true GB1077997A (en) | 1967-08-02 |
Family
ID=7097997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22364/64A Expired GB1077997A (en) | 1963-05-31 | 1964-05-29 | A process for the preparation of sulphur-containing derivatives of polymerization products of tetrahydrofuran |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1396855A (en) |
| GB (1) | GB1077997A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0374497A1 (en) * | 1988-11-29 | 1990-06-27 | BASF Aktiengesellschaft | Polybutanediol(1,4)w,w'bismercaptans and their preparation |
| EP0370445A3 (en) * | 1988-11-23 | 1990-07-04 | Ciba-Geigy Ag | Polytetrahydrofurandithiols and their use |
-
1964
- 1964-05-29 FR FR976344A patent/FR1396855A/en not_active Expired
- 1964-05-29 GB GB22364/64A patent/GB1077997A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0370445A3 (en) * | 1988-11-23 | 1990-07-04 | Ciba-Geigy Ag | Polytetrahydrofurandithiols and their use |
| EP0370446A3 (en) * | 1988-11-23 | 1990-07-11 | Ciba-Geigy Ag | Curable epoxy resin compositions containing polyalkylene dithiols and polyamines |
| US4990679A (en) * | 1988-11-23 | 1991-02-05 | Ciba-Geigy Corporation | Poly(tetrahydrofuran) |
| US5143999A (en) * | 1988-11-23 | 1992-09-01 | Ciba-Geigy Corporation | Hardenable mixtures of epoxide resin materials containing polyoxyalkylene-dithiols and polyamines |
| EP0374497A1 (en) * | 1988-11-29 | 1990-06-27 | BASF Aktiengesellschaft | Polybutanediol(1,4)w,w'bismercaptans and their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1396855A (en) | 1965-04-23 |
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