DE1128977B - Verwendung einer SH-Gruppen aufweisenden Fettsaeure oder eines Thiophenols als Loesungs- mittel fuer bestimmte Polymischester - Google Patents
Verwendung einer SH-Gruppen aufweisenden Fettsaeure oder eines Thiophenols als Loesungs- mittel fuer bestimmte PolymischesterInfo
- Publication number
- DE1128977B DE1128977B DEC17915A DEC0017915A DE1128977B DE 1128977 B DE1128977 B DE 1128977B DE C17915 A DEC17915 A DE C17915A DE C0017915 A DEC0017915 A DE C0017915A DE 1128977 B DE1128977 B DE 1128977B
- Authority
- DE
- Germany
- Prior art keywords
- thiophenol
- carbon atoms
- solvent
- groups
- solutions
- 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.)
- Pending
Links
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 title claims description 33
- 239000002904 solvent Substances 0.000 title claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 10
- 229930195729 fatty acid Natural products 0.000 title claims description 10
- 239000000194 fatty acid Substances 0.000 title claims description 10
- 150000004665 fatty acids Chemical class 0.000 title claims description 10
- 229920000728 polyester Polymers 0.000 title description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 15
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 12
- -1 aromatic dicarboxylic acids Chemical class 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 9
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000578 dry spinning Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002074 melt spinning Methods 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 238000002166 wet spinning Methods 0.000 description 2
- PWOBDMNCYMQTCE-UHFFFAOYSA-N 2-chlorobenzenethiol Chemical compound SC1=CC=CC=C1Cl PWOBDMNCYMQTCE-UHFFFAOYSA-N 0.000 description 1
- WBSONQUHDWJABP-UHFFFAOYSA-N 2-ethoxybenzenethiol Chemical compound CCOC1=CC=CC=C1S WBSONQUHDWJABP-UHFFFAOYSA-N 0.000 description 1
- KFFUEVDMVNIOHA-UHFFFAOYSA-N 3-aminobenzenethiol Chemical compound NC1=CC=CC(S)=C1 KFFUEVDMVNIOHA-UHFFFAOYSA-N 0.000 description 1
- WRXOZRLZDJAYDR-UHFFFAOYSA-N 3-methylbenzenethiol Chemical compound CC1=CC=CC(S)=C1 WRXOZRLZDJAYDR-UHFFFAOYSA-N 0.000 description 1
- MJPVYTKZYZPIQA-UHFFFAOYSA-N 3-thiophen-2-ylpropanoic acid Chemical compound OC(=O)CCC1=CC=CS1 MJPVYTKZYZPIQA-UHFFFAOYSA-N 0.000 description 1
- YUSDDNTYMDWOCY-UHFFFAOYSA-N 3-thiophen-3-ylpropanoic acid Chemical compound OC(=O)CCC=1C=CSC=1 YUSDDNTYMDWOCY-UHFFFAOYSA-N 0.000 description 1
- QICKSFILIHOSPO-UHFFFAOYSA-N 4-thiophen-3-ylbutanoic acid Chemical compound OC(=O)CCCC=1C=CSC=1 QICKSFILIHOSPO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZXPQAEWGZCFFDO-UHFFFAOYSA-N CCCCCCCCCCC(CC)CCCCCCC(C)C Chemical compound CCCCCCCCCCC(CC)CCCCCCC(C)C ZXPQAEWGZCFFDO-UHFFFAOYSA-N 0.000 description 1
- 239000012932 acetate dye Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- AHIOKFKBLGHSSV-UHFFFAOYSA-N diethyl hexadecanedioate Chemical compound CCOC(=O)CCCCCCCCCCCCCCC(=O)OCC AHIOKFKBLGHSSV-UHFFFAOYSA-N 0.000 description 1
- GBIBDFBIBIFTLW-UHFFFAOYSA-N dimethyl 8-ethyloctadecanedioate Chemical compound CCC(CCCCCCCCCC(=O)OC)CCCCCCC(=O)OC GBIBDFBIBIFTLW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
- C08J3/097—Sulfur containing 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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)
- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Artificial Filaments (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US698390A US2912405A (en) | 1957-11-25 | 1957-11-25 | Solutions of modified polyesters in thiol-substituted fatty acids |
| US698358A US2912404A (en) | 1957-11-25 | 1957-11-25 | Solutions of modified polyesters in thiophenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1128977B true DE1128977B (de) | 1962-05-03 |
Family
ID=27106196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC17915A Pending DE1128977B (de) | 1957-11-25 | 1958-11-24 | Verwendung einer SH-Gruppen aufweisenden Fettsaeure oder eines Thiophenols als Loesungs- mittel fuer bestimmte Polymischester |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US2912405A (en, 2012) |
| BE (1) | BE573284A (en, 2012) |
| CH (1) | CH402413A (en, 2012) |
| DE (1) | DE1128977B (en, 2012) |
| FR (1) | FR1215388A (en, 2012) |
| GB (1) | GB885522A (en, 2012) |
| NL (2) | NL110160C (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3260736A (en) * | 1960-12-20 | 1966-07-12 | Eastman Kodak Co | Preparation of thiolesters |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH295975A (de) * | 1951-10-18 | 1954-01-31 | Alexander Smith Inc | Vorrichtung zur Kräuselung von Fasern. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB712998A (en) * | 1950-06-29 | 1954-08-04 | British Celanese | Improvements in the production and use of acrylonitrile polymer solutions |
-
1957
- 1957-11-25 US US698390A patent/US2912405A/en not_active Expired - Lifetime
- 1957-11-25 US US698358A patent/US2912404A/en not_active Expired - Lifetime
-
1958
- 1958-11-11 GB GB36239/58A patent/GB885522A/en not_active Expired
- 1958-11-24 DE DEC17915A patent/DE1128977B/de active Pending
- 1958-11-25 BE BE573284A patent/BE573284A/xx unknown
- 1958-11-25 CH CH6656858A patent/CH402413A/de unknown
- 1958-11-25 NL NL233586A patent/NL110160C/xx active
- 1958-11-25 FR FR780036A patent/FR1215388A/fr not_active Expired
-
1964
- 1964-06-11 NL NL6406635A patent/NL125562C/xx active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH295975A (de) * | 1951-10-18 | 1954-01-31 | Alexander Smith Inc | Vorrichtung zur Kräuselung von Fasern. |
Also Published As
| Publication number | Publication date |
|---|---|
| US2912405A (en) | 1959-11-10 |
| US2912404A (en) | 1959-11-10 |
| NL125562C (en, 2012) | 1968-12-16 |
| BE573284A (en, 2012) | 1959-03-16 |
| CH402413A (de) | 1965-11-15 |
| NL110160C (en, 2012) | 1964-12-15 |
| FR1215388A (fr) | 1960-04-19 |
| GB885522A (en) | 1961-12-28 |
| NL6406635A (en, 2012) | 1964-08-10 |
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