GB1073640A - Method for preparing copolyesters - Google Patents
Method for preparing copolyestersInfo
- Publication number
- GB1073640A GB1073640A GB4269364A GB4269364A GB1073640A GB 1073640 A GB1073640 A GB 1073640A GB 4269364 A GB4269364 A GB 4269364A GB 4269364 A GB4269364 A GB 4269364A GB 1073640 A GB1073640 A GB 1073640A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glycol
- acid
- ester
- isophthalate
- mixture
- 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
- 229920001634 Copolyester Polymers 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 8
- 150000002148 esters Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 abstract 2
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 abstract 2
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 150000002739 metals Chemical class 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- MGIAHHJRDZCTHG-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 MGIAHHJRDZCTHG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001869 cobalt compounds Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000011133 lead Substances 0.000 abstract 1
- 229940046892 lead acetate Drugs 0.000 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
Terephthalate-isophthalate copolyesters are produced by esterifying isophthalic acid with a glycol to form a bis-glycol isophthalate having a low acid number (preferably below 10) and heating a mixture of this with a terephthalic ester and the glycol in the presence of an ester interchange catalyst to form a mixture of the glycol isophthalate and terephthalate, and then condensing this mixture to form high molecular weight linear polyesters. The acid number of the bis-glycol isophthalate may be reduced, if necessary, by treating the ester with a solid basic material insoluble therein, e.g. sodium carbonate, or by adding material which forms an insoluble precipitate with the acid components of the ester. The isophthalic acid may be reacted with the glycol in the presence of dialkyl terephthalate, if desired. Suitable esterification catalysts are glycol-soluble glycolates, alkoxides, weak acid salts, tertiary amines, amphoteric metals, metals of atomic number less than 26, p-toluene sulphonic acid, acetic anhydride and sulphuric acid. Suitable ester interchange catalysts are the acetates of lead, zinc or manganese, and litharge, and condensation catalysts may be antimony trioxide, litharge, lead acetate and glycol-soluble titanium and cobalt compounds.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32575363A | 1963-11-22 | 1963-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1073640A true GB1073640A (en) | 1967-06-28 |
Family
ID=23269296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4269364A Expired GB1073640A (en) | 1963-11-22 | 1964-10-20 | Method for preparing copolyesters |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT276769B (en) |
| GB (1) | GB1073640A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0103531A1 (en) * | 1982-09-07 | 1984-03-21 | The Goodyear Tire & Rubber Company | Polyethylene isophthalate having reduced cyclic dimer content and process therefor |
| ES2162737A1 (en) * | 1999-07-30 | 2002-01-01 | Univ Catalunya Politecnica | Set of high thermal stability polycondensation copolymers consists of copolyesters based on terephthalate and tetrabutoxide catalyst, more heat resistant than PET |
| US8148278B2 (en) | 2003-06-19 | 2012-04-03 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8178199B2 (en) | 2003-06-19 | 2012-05-15 | Eastman Chemical Company | Nonwovens produced from multicomponent fibers |
| US8216953B2 (en) | 2003-06-19 | 2012-07-10 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8512519B2 (en) | 2009-04-24 | 2013-08-20 | Eastman Chemical Company | Sulfopolyesters for paper strength and process |
| US8840758B2 (en) | 2012-01-31 | 2014-09-23 | Eastman Chemical Company | Processes to produce short cut microfibers |
| US9273417B2 (en) | 2010-10-21 | 2016-03-01 | Eastman Chemical Company | Wet-Laid process to produce a bound nonwoven article |
| US9303357B2 (en) | 2013-04-19 | 2016-04-05 | Eastman Chemical Company | Paper and nonwoven articles comprising synthetic microfiber binders |
| US9598802B2 (en) | 2013-12-17 | 2017-03-21 | Eastman Chemical Company | Ultrafiltration process for producing a sulfopolyester concentrate |
| US9605126B2 (en) | 2013-12-17 | 2017-03-28 | Eastman Chemical Company | Ultrafiltration process for the recovery of concentrated sulfopolyester dispersion |
-
1964
- 1964-10-20 GB GB4269364A patent/GB1073640A/en not_active Expired
- 1964-11-16 AT AT966464A patent/AT276769B/en not_active IP Right Cessation
Cited By (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0103531A1 (en) * | 1982-09-07 | 1984-03-21 | The Goodyear Tire & Rubber Company | Polyethylene isophthalate having reduced cyclic dimer content and process therefor |
| ES2162737A1 (en) * | 1999-07-30 | 2002-01-01 | Univ Catalunya Politecnica | Set of high thermal stability polycondensation copolymers consists of copolyesters based on terephthalate and tetrabutoxide catalyst, more heat resistant than PET |
| US8444895B2 (en) | 2003-06-19 | 2013-05-21 | Eastman Chemical Company | Processes for making water-dispersible and multicomponent fibers from sulfopolyesters |
| US8444896B2 (en) | 2003-06-19 | 2013-05-21 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8163385B2 (en) | 2003-06-19 | 2012-04-24 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8178199B2 (en) | 2003-06-19 | 2012-05-15 | Eastman Chemical Company | Nonwovens produced from multicomponent fibers |
| US8216953B2 (en) | 2003-06-19 | 2012-07-10 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8227362B2 (en) | 2003-06-19 | 2012-07-24 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8236713B2 (en) | 2003-06-19 | 2012-08-07 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8247335B2 (en) | 2003-06-19 | 2012-08-21 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8257628B2 (en) | 2003-06-19 | 2012-09-04 | Eastman Chemical Company | Process of making water-dispersible multicomponent fibers from sulfopolyesters |
| US8262958B2 (en) | 2003-06-19 | 2012-09-11 | Eastman Chemical Company | Process of making woven articles comprising water-dispersible multicomponent fibers |
| US8691130B2 (en) | 2003-06-19 | 2014-04-08 | Eastman Chemical Company | Process of making water-dispersible multicomponent fibers from sulfopolyesters |
| US8277706B2 (en) | 2003-06-19 | 2012-10-02 | Eastman Chemical Company | Process of making water-dispersible multicomponent fibers from sulfopolyesters |
| US8314041B2 (en) | 2003-06-19 | 2012-11-20 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8388877B2 (en) | 2003-06-19 | 2013-03-05 | Eastman Chemical Company | Process of making water-dispersible multicomponent fibers from sulfopolyesters |
| US8398907B2 (en) | 2003-06-19 | 2013-03-19 | Eastman Chemical Company | Process of making water-dispersible multicomponent fibers from sulfopolyesters |
| US8435908B2 (en) | 2003-06-19 | 2013-05-07 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8158244B2 (en) | 2003-06-19 | 2012-04-17 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8148278B2 (en) | 2003-06-19 | 2012-04-03 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8273451B2 (en) | 2003-06-19 | 2012-09-25 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8513147B2 (en) | 2003-06-19 | 2013-08-20 | Eastman Chemical Company | Nonwovens produced from multicomponent fibers |
| US8557374B2 (en) | 2003-06-19 | 2013-10-15 | Eastman Chemical Company | Water-dispersible and multicomponent fibers from sulfopolyesters |
| US8623247B2 (en) | 2003-06-19 | 2014-01-07 | Eastman Chemical Company | Process of making water-dispersible multicomponent fibers from sulfopolyesters |
| US8512519B2 (en) | 2009-04-24 | 2013-08-20 | Eastman Chemical Company | Sulfopolyesters for paper strength and process |
| US9273417B2 (en) | 2010-10-21 | 2016-03-01 | Eastman Chemical Company | Wet-Laid process to produce a bound nonwoven article |
| US8840758B2 (en) | 2012-01-31 | 2014-09-23 | Eastman Chemical Company | Processes to produce short cut microfibers |
| US8840757B2 (en) | 2012-01-31 | 2014-09-23 | Eastman Chemical Company | Processes to produce short cut microfibers |
| US8871052B2 (en) | 2012-01-31 | 2014-10-28 | Eastman Chemical Company | Processes to produce short cut microfibers |
| US8882963B2 (en) | 2012-01-31 | 2014-11-11 | Eastman Chemical Company | Processes to produce short cut microfibers |
| US8906200B2 (en) | 2012-01-31 | 2014-12-09 | Eastman Chemical Company | Processes to produce short cut microfibers |
| US9175440B2 (en) | 2012-01-31 | 2015-11-03 | Eastman Chemical Company | Processes to produce short-cut microfibers |
| US9303357B2 (en) | 2013-04-19 | 2016-04-05 | Eastman Chemical Company | Paper and nonwoven articles comprising synthetic microfiber binders |
| US9617685B2 (en) | 2013-04-19 | 2017-04-11 | Eastman Chemical Company | Process for making paper and nonwoven articles comprising synthetic microfiber binders |
| US9598802B2 (en) | 2013-12-17 | 2017-03-21 | Eastman Chemical Company | Ultrafiltration process for producing a sulfopolyester concentrate |
| US9605126B2 (en) | 2013-12-17 | 2017-03-28 | Eastman Chemical Company | Ultrafiltration process for the recovery of concentrated sulfopolyester dispersion |
Also Published As
| Publication number | Publication date |
|---|---|
| AT276769B (en) | 1969-12-10 |
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