CA1059248A - Water soluble polyrethane - Google Patents
Water soluble polyrethaneInfo
- Publication number
- CA1059248A CA1059248A CA239,686A CA239686A CA1059248A CA 1059248 A CA1059248 A CA 1059248A CA 239686 A CA239686 A CA 239686A CA 1059248 A CA1059248 A CA 1059248A
- Authority
- CA
- Canada
- Prior art keywords
- polyester
- diisocyanate
- polyurethane
- new
- diacid
- 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
- 239000004814 polyurethane Substances 0.000 title claims abstract description 26
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 26
- 229920000728 polyester Polymers 0.000 claims abstract description 25
- 125000000129 anionic group Chemical group 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000004753 textile Substances 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 235000011037 adipic acid Nutrition 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 238000004026 adhesive bonding Methods 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims 1
- 150000001279 adipic acids Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 238000004513 sizing Methods 0.000 abstract description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 9
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000001361 adipic acid Substances 0.000 description 6
- 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 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000003292 glue Substances 0.000 description 4
- 238000009941 weaving Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KFMQPIHLHGRTFB-UHFFFAOYSA-L disodium;2,2-dimethyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)C(C)(C)C(C([O-])=O)S(O)(=O)=O KFMQPIHLHGRTFB-UHFFFAOYSA-L 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- -1 ethyl diesters Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- NLKKMQOPDZTBTA-UHFFFAOYSA-N 1,6-diisocyanatooctane Chemical compound O=C=NC(CC)CCCCCN=C=O NLKKMQOPDZTBTA-UHFFFAOYSA-N 0.000 description 1
- HTXMGVTWXZBZNC-UHFFFAOYSA-N 3,5-bis(methoxycarbonyl)benzenesulfonic acid Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(S(O)(=O)=O)=C1 HTXMGVTWXZBZNC-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- HXRDIZJXWOAWGI-UHFFFAOYSA-N [Na+].O[S-](=O)=O Chemical compound [Na+].O[S-](=O)=O HXRDIZJXWOAWGI-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MHKKFFHWMKEBDW-UHFFFAOYSA-N dimethyl 2,5-dioxocyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CC(=O)C(C(=O)OC)CC1=O MHKKFFHWMKEBDW-UHFFFAOYSA-N 0.000 description 1
- RXQGGECQTVPOOB-UHFFFAOYSA-L disodium 4,6-dimethyl-2-sulfobenzene-1,3-dicarboxylate Chemical compound CC1=CC(=C(C(=C1C(=O)[O-])S(=O)(=O)O)C(=O)[O-])C.[Na+].[Na+] RXQGGECQTVPOOB-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4676—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing sulfur
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/572—Reaction products of isocyanates with polyesters or polyesteramides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Textile Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7436705A FR2290460A1 (fr) | 1974-11-05 | 1974-11-05 | Procede de fabrication de polyurethannes hydrosolubles |
| AR260740A AR207788A1 (es) | 1974-11-05 | 1975-01-01 | Poliuretanos hidrosolubles |
| BR7506845*A BR7506845A (pt) | 1974-11-05 | 1975-10-20 | Poliuretano hidrossoluvel |
| GB45338/75A GB1483687A (en) | 1974-11-05 | 1975-10-31 | Water-soluble polyurethanes |
| LU73707A LU73707A1 (enExample) | 1974-11-05 | 1975-11-03 | |
| BE161579A BE835243A (fr) | 1974-11-05 | 1975-11-04 | Nouveaux polyurethanne hydrosoluble |
| CH1420975A CH612305GA3 (en) | 1974-11-05 | 1975-11-04 | Use of a new water-soluble polyurethane for sizing textile yarns |
| NLAANVRAGE7512919,A NL181363C (nl) | 1974-11-05 | 1975-11-04 | Werkwijze voor het bereiden van in water oplosbare polyurethanen; werkwijze voor het lijmen van textieldraden alsmede weefsels vervaardigd onder toepassing van aldus gelijmde textieldraden. |
| AT838575A AT342310B (de) | 1974-11-05 | 1975-11-04 | Verfahren zur herstellung von neuen polyurethanen |
| CH263677A CH611913A5 (en) | 1974-11-05 | 1975-11-04 | Process for the preparation of a water-soluble polyurethane |
| DK495075A DK495075A (da) | 1974-11-05 | 1975-11-04 | Vandoploselige polyurethaner |
| DE2549623A DE2549623C3 (de) | 1974-11-05 | 1975-11-05 | Wasserlösliches Polyurethan und seine Verwendung |
| CA239,686A CA1059248A (fr) | 1974-11-05 | 1975-11-14 | Water soluble polyrethane |
| AT0475477A AT375414B (de) | 1974-11-05 | 1977-07-04 | Verwendung eines neuen polyurethans zum schlichten von textilgarnen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7436705A FR2290460A1 (fr) | 1974-11-05 | 1974-11-05 | Procede de fabrication de polyurethannes hydrosolubles |
| CA239,686A CA1059248A (fr) | 1974-11-05 | 1975-11-14 | Water soluble polyrethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1059248A true CA1059248A (fr) | 1979-07-24 |
Family
ID=25668139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,686A Expired CA1059248A (fr) | 1974-11-05 | 1975-11-14 | Water soluble polyrethane |
Country Status (12)
| Country | Link |
|---|---|
| AR (1) | AR207788A1 (enExample) |
| AT (1) | AT342310B (enExample) |
| BE (1) | BE835243A (enExample) |
| BR (1) | BR7506845A (enExample) |
| CA (1) | CA1059248A (enExample) |
| CH (2) | CH612305GA3 (enExample) |
| DE (1) | DE2549623C3 (enExample) |
| DK (1) | DK495075A (enExample) |
| FR (1) | FR2290460A1 (enExample) |
| GB (1) | GB1483687A (enExample) |
| LU (1) | LU73707A1 (enExample) |
| NL (1) | NL181363C (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2734102A1 (de) * | 1977-07-28 | 1979-02-15 | Bayer Ag | Verfahren zur herstellung von dihydroxypolyurethanen und ihre verwendung als klebstoff oder als klebstoffrohstoff |
| US4307219A (en) * | 1980-04-30 | 1981-12-22 | Minnesota Mining And Manufacturing Company | Aqueous solvent dispersible linear polyurethane resins |
| NL8220284A (nl) * | 1981-08-19 | 1983-07-01 | Sony Corp | Door elektronenstraling hardbare hars. |
| US4738992A (en) * | 1985-12-09 | 1988-04-19 | Minnesota Mining And Manufacturing Company | Hydrophilic polyurethane/polyurea sponge |
| US4638017A (en) * | 1985-12-09 | 1987-01-20 | Minnesota Mining And Manufacturing Company | Hydrophilic polyurethane/polyurea sponge |
| GB2235927B (en) * | 1989-09-14 | 1992-10-21 | Asahi Chemical Ind | A sulfonic acid group-containing polyurethane and a photosensitive resin composition containing the same |
| GB9311139D0 (en) * | 1993-05-28 | 1993-07-14 | Zeneca Resins Bv | Aqueous crosslinkable coating compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1499121A (enExample) * | 1964-12-08 | 1968-01-12 | ||
| DE1570615C3 (de) * | 1965-10-16 | 1975-05-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von dispergierbaren Polyurethanen |
-
1974
- 1974-11-05 FR FR7436705A patent/FR2290460A1/fr active Granted
-
1975
- 1975-01-01 AR AR260740A patent/AR207788A1/es active
- 1975-10-20 BR BR7506845*A patent/BR7506845A/pt unknown
- 1975-10-31 GB GB45338/75A patent/GB1483687A/en not_active Expired
- 1975-11-03 LU LU73707A patent/LU73707A1/xx unknown
- 1975-11-04 NL NLAANVRAGE7512919,A patent/NL181363C/xx not_active IP Right Cessation
- 1975-11-04 DK DK495075A patent/DK495075A/da not_active Application Discontinuation
- 1975-11-04 AT AT838575A patent/AT342310B/de not_active IP Right Cessation
- 1975-11-04 CH CH1420975A patent/CH612305GA3/xx not_active IP Right Cessation
- 1975-11-04 BE BE161579A patent/BE835243A/xx not_active IP Right Cessation
- 1975-11-04 CH CH263677A patent/CH611913A5/xx not_active IP Right Cessation
- 1975-11-05 DE DE2549623A patent/DE2549623C3/de not_active Expired
- 1975-11-14 CA CA239,686A patent/CA1059248A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL181363C (nl) | 1987-08-03 |
| DE2549623C3 (de) | 1981-05-14 |
| BR7506845A (pt) | 1976-08-10 |
| ATA838575A (de) | 1977-07-15 |
| AT342310B (de) | 1978-03-28 |
| NL181363B (nl) | 1987-03-02 |
| CH612305GA3 (en) | 1979-07-31 |
| DK495075A (da) | 1976-05-06 |
| FR2290460A1 (fr) | 1976-06-04 |
| DE2549623B2 (de) | 1980-07-31 |
| AR207788A1 (es) | 1976-10-29 |
| GB1483687A (en) | 1977-08-24 |
| FR2290460B1 (enExample) | 1979-03-16 |
| NL7512919A (nl) | 1976-05-07 |
| CH612305B (fr) | |
| DE2549623A1 (de) | 1976-05-06 |
| CH611913A5 (en) | 1979-06-29 |
| LU73707A1 (enExample) | 1977-02-09 |
| BE835243A (fr) | 1976-05-04 |
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