CA1096534A - Polyesters having unobvious weatherability characteristics - Google Patents
Polyesters having unobvious weatherability characteristicsInfo
- Publication number
- CA1096534A CA1096534A CA313,211A CA313211A CA1096534A CA 1096534 A CA1096534 A CA 1096534A CA 313211 A CA313211 A CA 313211A CA 1096534 A CA1096534 A CA 1096534A
- Authority
- CA
- Canada
- Prior art keywords
- polyester
- mole percent
- carbon atoms
- cyclohexanedimethanol
- terephthalic acid
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/132—Phenols containing keto groups, e.g. benzophenones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
Abstract
POLYESTERS HAVING UNOBVIOUS WEATHERABILITY CHARACTERISTICS
Abstract of the Disclosure Disclosed is a composition consisting essentially of a stabilize-and a polyester of terephthalic acid, 1,4-cyclohexanedimethanol and a critical range of either ethylene glycol, 1,4-butanediol or 2,2-dimethyl-1,3-propanediol. These compositions have an unobvious resistance to weathering.
Abstract of the Disclosure Disclosed is a composition consisting essentially of a stabilize-and a polyester of terephthalic acid, 1,4-cyclohexanedimethanol and a critical range of either ethylene glycol, 1,4-butanediol or 2,2-dimethyl-1,3-propanediol. These compositions have an unobvious resistance to weathering.
Description
~6~34 This invention relates to polyester compositions which have a markedly enhanced resistance to weathering.
Broadly, these compositions can be thought of as an admixture of a stabilizer and a polyester. The stabilizer can be one of three specific types and the polyester can be one of three specific types.
The rirst polyester is compris2d of terephthalic acid, 1 to ;0 mole percent ethylene giycol, and 99 to 50 mole ?ercent 1,4-cvclohex~ne-dimelhar.ol .
The second polyester is comprised of terephthalic acid, 1 to 50 mole percent 1,4-butanediol and 99 to 50 mole percent 1,4-cyclo-hexanedimethanol.
The third polyester is comprised of terephthaiic acid, I to 50 mole percent 2,2-dimethyl-1,3-propanediol, and 99 to 50 mole percent ` 1,4-cyclohexanedimethanol.
The first type of stabilizer is a 2-hydroxyphenyl benzotriazole type stabilizer corresponding to the structure ~ R~ ~herein ~1 Rl is a monovalent alkyl radical having 1 tc 18 carbon âtO...S.
and R2 is -H, -Cl or a monovalent alkyl radical having 1 to 18 carbon atoms.
~ xamples of monovalent alkyl radicals having 1 to 1~ carbGn atoms includes methyl, ethyl, n-propyl, n-butyl, tertiary butyl, 2, -dimethylbutyl, 2,2-dimethylhexyl, n-pentyl, n-hexyl, 2-ethylhexyl, n-octyl, 2,2-dimethyloctyl, n-nonyl, n-decyl, dodecyl, 2,2-dimethyldecyl, stearyl, and the like.
30 A preferred species corresponds to the structure _ ~ -~3~3 t~ il ~ H3 and can be called 2-(2H-benzotriazol-2-yl)-p-cresol. This compound is sold commercially under the name Tinuvin P by Ciba Geigy Chemical Corpo~ation.
These compounds and thelr preparation are wel' knowr. -n the art and are described in U.S. 3,004,896.
The second type of stabilizer is a 2-hydroxy benzophenone type stabilizer correspo~ding to the structure F~3 qH
R3-0~ -R~ wherein R3 is -H, -OH, -Cl or an alkoxy group having 1 to 18 carbon atoms, with the proviso that at least one R3 must be either -OH or alkoxy.
Examples of alkoxy groups having 1 to 18 carbon atoms are methyloxy, e~hyloxy, n-butyloxy, 2,2-dimethylhexyloxy, n-pentyloxy, 2-ethylhexyloxy, heptyloxy, n-octyloxy, 2,2-dimethyldecyloxy, dodecyloxy, ant the llke.
A preferred species corresponds to the structure ,0~1 ~ OC12H2s and can be called 4-(dodecyloxy)-2-hydroxybenzophenone. This co~ound is sold commerclally under the name ~astman Inhibitor DO~P by Eastman Che~ical Products, Inc.
These compounds and their preparation are well known in the art and are described in U.S. 2,861,053.
The third type of stabilizer is a substituted ethylene type 3tabilizer corre6pondin~ to the structure 3~
R7~ C~`4 wherein ~9 \R4 R4 is -C~ or an alkyl acyloxy group having 1 to 8 carbon atoms in the alkyl portion, R5 is -~, a monovalent alkyl radical having 1 to 8 carbon atoms or a phenyl radical, ~6 is -H, -Cl, a mono~alent alkyl radic~l having i to 8 carDcn atoms or an alkyl acylo-xy group h~ving 1 to 8 carbon atcms in the alkyl portion, and R7 is an alkoxy group having 1 ~o 18 carbon atoms, a benzylo-.cy group or a phenoxy Eroup.
Examples of monovalent alkyl radicals having 1 .o .~ carbon atoms that can form the alkyl portion of the alkyl acyloxy group are methyl, ethyl, n-propyl, n-butyl, 2,2-dimethylbutyl, 2,2-dimethylhexyl, n-pentyl, n-hexyl, 2-ethylhexyl and n-octyl.
Examples of monovalent al~yl radicals having 1 to 8 carbon atoms are methyl, ethyl, n-propyl, n-butyl, 2,2-dimethylbutyl, 2,2-dimethylhexyl, n-pentyl, n-hexyl, 2-ethylhexyl and n-octyl.
: Examples of alkoxy groups having 1 to 18 carbon atoms are ~20 methyloxy, ethyloxy, n-butyloxy, 2,2-dimethylhexyloxy, n-pentyloxy, ethylhexyloxy, n-octyloxy; 2,2-d~methyldecylo~y, and the like.
A preferred species corresponds to the structure ~ -OCH3 CH30-a~ ~CH=C
~= o \~CH 3 which can be called dimethgl p-methoxYbenzylidene~alonate. This compound - is sold co~mercially as Cyasorb ~ 88 by American Cyanamid Co.
These compounds and their preparation are well known in the art and are described in U.S. 3,706,701.
The compositions of this invention are described as "consisting e~sentially of" the polyester and the stabilizer. By this term we mean ~L1)5~6S3~
these polyesters can contain other materials as long as the unobvious weatherability properties are retained. For example, other dicarboxy'ic acids and diols could be used if the resulting polyester retains the unobvious weatherability properties of the polyester of the invention.
Examples of other dicarboxylic acids include isophthalic, adipic, azelaic, succinic, glutaric and 2,6-naphthalene dicarboxylic acid. Also, conven-tional additives for molded articles, such as antioxidants, other stabilizers, plasticizers, pigments, flame retardants, ar.d the llke can be incorporated into the composition of this invention as long as the polyester retains unobvious weatherability properties.
The polyesters useful in this invention have an inherent viscosity of at least 0.5, preferably at least 0.7 when measured at 25C. using 0.50 grams of polymer per 100 ml. of a solvent composed of 60 volumes of phenol and 40 volumes of tetrachloroethane.
The polyesters of this invention are broadly known and can be prepared by a variety of processes such as direct condensation, acidolysis, and ester interchange. Preferably the polyester is prepared by ester interchange where the dimethyl ester of terephthalic acid and the two glycols are reacted to form a mixture of the bis esters of the two glycois and the mixture of bis esters is polycondensed at high temperature and low pressure to form a high molecular weight polymer through elimin2t-0n of the two glycols.
In this invention the range of the other glycol besides 1,4-cyclohexanedimethanol is broadly 1 to 50, preferably 5 to 40 mole per-cent. Obviously, the remaining moies of 1,4 cyclohexanedimethanol would be 99 to 50, preferably 95 to 60 mole percent.
The admixture of the polyester and the stabilizer can be for~ed using technology well known in the art. For example, pellets of the polyester can be coated with powdered stabilizer and extruded.
Preferably, the stabilizer is coextruded from the polymerization reactor ; wherein the polyester is formed.
Broadly, the amount of stabilizer can be an amount sufficient ~D9~iS34 to achieve enhanced weatherability. In one embodiment the amount cf stabilizer can be 0.1 to 5.0 weight percent, based on the weight of the polyester. Preferably, 0.25 to 2.0 weight percent can be used.
The polyester of this invention can be prepared into useful articles, such as window panes, by conventional extrusion equipment and procedures.
Broadly, these compositions can be thought of as an admixture of a stabilizer and a polyester. The stabilizer can be one of three specific types and the polyester can be one of three specific types.
The rirst polyester is compris2d of terephthalic acid, 1 to ;0 mole percent ethylene giycol, and 99 to 50 mole ?ercent 1,4-cvclohex~ne-dimelhar.ol .
The second polyester is comprised of terephthalic acid, 1 to 50 mole percent 1,4-butanediol and 99 to 50 mole percent 1,4-cyclo-hexanedimethanol.
The third polyester is comprised of terephthaiic acid, I to 50 mole percent 2,2-dimethyl-1,3-propanediol, and 99 to 50 mole percent ` 1,4-cyclohexanedimethanol.
The first type of stabilizer is a 2-hydroxyphenyl benzotriazole type stabilizer corresponding to the structure ~ R~ ~herein ~1 Rl is a monovalent alkyl radical having 1 tc 18 carbon âtO...S.
and R2 is -H, -Cl or a monovalent alkyl radical having 1 to 18 carbon atoms.
~ xamples of monovalent alkyl radicals having 1 to 1~ carbGn atoms includes methyl, ethyl, n-propyl, n-butyl, tertiary butyl, 2, -dimethylbutyl, 2,2-dimethylhexyl, n-pentyl, n-hexyl, 2-ethylhexyl, n-octyl, 2,2-dimethyloctyl, n-nonyl, n-decyl, dodecyl, 2,2-dimethyldecyl, stearyl, and the like.
30 A preferred species corresponds to the structure _ ~ -~3~3 t~ il ~ H3 and can be called 2-(2H-benzotriazol-2-yl)-p-cresol. This compound is sold commercially under the name Tinuvin P by Ciba Geigy Chemical Corpo~ation.
These compounds and thelr preparation are wel' knowr. -n the art and are described in U.S. 3,004,896.
The second type of stabilizer is a 2-hydroxy benzophenone type stabilizer correspo~ding to the structure F~3 qH
R3-0~ -R~ wherein R3 is -H, -OH, -Cl or an alkoxy group having 1 to 18 carbon atoms, with the proviso that at least one R3 must be either -OH or alkoxy.
Examples of alkoxy groups having 1 to 18 carbon atoms are methyloxy, e~hyloxy, n-butyloxy, 2,2-dimethylhexyloxy, n-pentyloxy, 2-ethylhexyloxy, heptyloxy, n-octyloxy, 2,2-dimethyldecyloxy, dodecyloxy, ant the llke.
A preferred species corresponds to the structure ,0~1 ~ OC12H2s and can be called 4-(dodecyloxy)-2-hydroxybenzophenone. This co~ound is sold commerclally under the name ~astman Inhibitor DO~P by Eastman Che~ical Products, Inc.
These compounds and their preparation are well known in the art and are described in U.S. 2,861,053.
The third type of stabilizer is a substituted ethylene type 3tabilizer corre6pondin~ to the structure 3~
R7~ C~`4 wherein ~9 \R4 R4 is -C~ or an alkyl acyloxy group having 1 to 8 carbon atoms in the alkyl portion, R5 is -~, a monovalent alkyl radical having 1 to 8 carbon atoms or a phenyl radical, ~6 is -H, -Cl, a mono~alent alkyl radic~l having i to 8 carDcn atoms or an alkyl acylo-xy group h~ving 1 to 8 carbon atcms in the alkyl portion, and R7 is an alkoxy group having 1 ~o 18 carbon atoms, a benzylo-.cy group or a phenoxy Eroup.
Examples of monovalent alkyl radicals having 1 .o .~ carbon atoms that can form the alkyl portion of the alkyl acyloxy group are methyl, ethyl, n-propyl, n-butyl, 2,2-dimethylbutyl, 2,2-dimethylhexyl, n-pentyl, n-hexyl, 2-ethylhexyl and n-octyl.
Examples of monovalent al~yl radicals having 1 to 8 carbon atoms are methyl, ethyl, n-propyl, n-butyl, 2,2-dimethylbutyl, 2,2-dimethylhexyl, n-pentyl, n-hexyl, 2-ethylhexyl and n-octyl.
: Examples of alkoxy groups having 1 to 18 carbon atoms are ~20 methyloxy, ethyloxy, n-butyloxy, 2,2-dimethylhexyloxy, n-pentyloxy, ethylhexyloxy, n-octyloxy; 2,2-d~methyldecylo~y, and the like.
A preferred species corresponds to the structure ~ -OCH3 CH30-a~ ~CH=C
~= o \~CH 3 which can be called dimethgl p-methoxYbenzylidene~alonate. This compound - is sold co~mercially as Cyasorb ~ 88 by American Cyanamid Co.
These compounds and their preparation are well known in the art and are described in U.S. 3,706,701.
The compositions of this invention are described as "consisting e~sentially of" the polyester and the stabilizer. By this term we mean ~L1)5~6S3~
these polyesters can contain other materials as long as the unobvious weatherability properties are retained. For example, other dicarboxy'ic acids and diols could be used if the resulting polyester retains the unobvious weatherability properties of the polyester of the invention.
Examples of other dicarboxylic acids include isophthalic, adipic, azelaic, succinic, glutaric and 2,6-naphthalene dicarboxylic acid. Also, conven-tional additives for molded articles, such as antioxidants, other stabilizers, plasticizers, pigments, flame retardants, ar.d the llke can be incorporated into the composition of this invention as long as the polyester retains unobvious weatherability properties.
The polyesters useful in this invention have an inherent viscosity of at least 0.5, preferably at least 0.7 when measured at 25C. using 0.50 grams of polymer per 100 ml. of a solvent composed of 60 volumes of phenol and 40 volumes of tetrachloroethane.
The polyesters of this invention are broadly known and can be prepared by a variety of processes such as direct condensation, acidolysis, and ester interchange. Preferably the polyester is prepared by ester interchange where the dimethyl ester of terephthalic acid and the two glycols are reacted to form a mixture of the bis esters of the two glycois and the mixture of bis esters is polycondensed at high temperature and low pressure to form a high molecular weight polymer through elimin2t-0n of the two glycols.
In this invention the range of the other glycol besides 1,4-cyclohexanedimethanol is broadly 1 to 50, preferably 5 to 40 mole per-cent. Obviously, the remaining moies of 1,4 cyclohexanedimethanol would be 99 to 50, preferably 95 to 60 mole percent.
The admixture of the polyester and the stabilizer can be for~ed using technology well known in the art. For example, pellets of the polyester can be coated with powdered stabilizer and extruded.
Preferably, the stabilizer is coextruded from the polymerization reactor ; wherein the polyester is formed.
Broadly, the amount of stabilizer can be an amount sufficient ~D9~iS34 to achieve enhanced weatherability. In one embodiment the amount cf stabilizer can be 0.1 to 5.0 weight percent, based on the weight of the polyester. Preferably, 0.25 to 2.0 weight percent can be used.
The polyester of this invention can be prepared into useful articles, such as window panes, by conventional extrusion equipment and procedures.
Claims (7)
1. A composition consisting essentially of an admixture of (A) a polyester having an inherent viscosity of at least 0.5 selected from the group consisting of (1) a polyester of terephthalic acid, 1 to 50 mole percent ethylene glycol and 99 to 50 mole percent 1,4-cyclohexanedimethanol, (2) a polyester of terephthalic acid, 1 to 50 mole percent 1,4-butanediol and 99 to 50 mole percent 1,4-cyclohexanedimethanol, and (3) a polyester of terephthalic acid, 1 to 50 mole per-cent 2,2-dimethyl-1,3-propanediol and 99 to 50 mole percent 1,4-cyclohexanedimethanol, (B) stabilizing quantities of a stabilizer selected from the group consisting of (1) 2-hydroxyphenyl benzotriazole type stabilizers corresponding to the structure wherein R1 is a monovalent alkyl radical having 1 to 18 carbon atoms, R2 is -H, -Cl or a monovalent alkyl radical having 1 to 18 carbon atoms, (2) 2-hydroxy benzophenone type stabilizers correspond-ing to the structure wherein R3 is -H, -OH, -Cl or an alkoxy group having 1 to 18 carbon atoms, with the proviso that at least one R3 must be either -OH or alkoxy, and (3) substituted ethylene type stabilizers corresponding to the structure wherein R4 is -CN or an alkyl acyloxy group having 1 to 8 carbon atoms in the alkyl portion, R5 is -H, a monovalent alkyl radical having 1 to 8 carbon atoms or a phenyl radical, R6 is -H, -Cl, a monovalent alkyl radical having 1 to 8 carbon atoms or an alkyl acyloxy group having 1 to 8 carbon atoms in the alkyl portion, and R7 is an alkoxy group having 1 to 18 carbon atoms, a benzyloxy group or a phenoxy group.
2. The composition of Claim 1 wherein the inherent viscosity is at least 0.7.
3. The composition of Claim 1 wherein the polyester of part (A)(1) is a polyester of terephthalic acid, 5 to 40 mole percent ethylene glycol and 95 to 60 mole percent 1,4-cyclohexanedimethanol.
4. The composition of Claim 1 wherein the polyester of part (A)(2) is a polyester of terephthalic acid, 5 to 40 mole percent 1,4-butanediol and 95 to 60 mole percent 1,4-cyclohexanedimethanol.
5. The composition of Claim 1 wherein the 2-hydroxyphenyl benzotriazole type stabilizer corresponds to the structure , the 2-hydroxy benzophenone type stabilizer corresponds to the structure , and the substituted ethylene type stabilizer corresponds to the structure .
6. The composition of Claim 1 wherein the quantity of stabilizer is 0.1 to 5.0 weight percent, based on the weight of the polyester.
7. A composition consisting essentially of an admixture of (A) a polyester having an inherent viscosity of at least 0.7 selected from the group consisting of (1) a polyester of terephthalic acid, 5 to 40 mole per-cent ethylene glycol and 95 to 60 mole percent 1,4-cyclohexanedimethanol, and (2) a polyester of terephthalic acid, 5 to 40 mole per-cent 1,4-butanediol and 95 to 60 mole percent 1,4-cyclohexanedimethanol, and (B) 0.25 to 2.0 weight percent, based on the weight of the polyester, of a 2-hydroxyphenyl benzotriazole type stabilizer corresponding to the structure .
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85977477A | 1977-12-12 | 1977-12-12 | |
| US859,774 | 1977-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1096534A true CA1096534A (en) | 1981-02-24 |
Family
ID=25331678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA313,211A Expired CA1096534A (en) | 1977-12-12 | 1978-10-12 | Polyesters having unobvious weatherability characteristics |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5488954A (en) |
| CA (1) | CA1096534A (en) |
| DE (1) | DE2853631A1 (en) |
| GB (1) | GB2009768B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5709929A (en) * | 1992-10-26 | 1998-01-20 | Axxis N.V. | Plastic sheet, a process for the manufacture thereof and formed articles containing the sheet |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0322557A1 (en) * | 1987-12-31 | 1989-07-05 | General Electric Company | Improved process and composition for surface impregnation of thermoplastic polymers with UV-absorbing compounds |
| JPH0229453A (en) * | 1988-07-18 | 1990-01-31 | Toray Ind Inc | Thermoplastic polyester resin composition |
| US5032631A (en) * | 1988-11-10 | 1991-07-16 | Hoechst Celanese Corporation | UV-light stabilized polyester molding compositions |
| US4937026A (en) * | 1988-12-16 | 1990-06-26 | General Electric Company | Method of surface impregnating hot polycarbonate sheet with an ultraviolet radiation screener composition |
| US5610049A (en) * | 1991-05-01 | 1997-03-11 | The Wistar Institute Of Anatomy And Biology | Human rotavirus HCR3A and method of growing said rotavirus |
| KR100209818B1 (en) * | 1992-09-04 | 1999-07-15 | 사또 아끼오 | Degradable adhesive film and degradable resin composition |
| US5480926A (en) * | 1995-04-28 | 1996-01-02 | Eastman Chemical Company | Blends of ultraviolet absorbers and polyesters |
| DE19522118C1 (en) * | 1995-06-19 | 1997-03-13 | Hoechst Ag | Amorphous, transparent, UV-stabilized plate made of a crystallizable thermoplastic, process for its production and its use |
| DE19642286A1 (en) * | 1996-10-14 | 1998-04-30 | Hoechst Ag | Amorphous, UV-stabilized, crystallizable plate and a crystallized molded body producible therefrom with a high and uniform heat resistance |
| US6001952A (en) * | 1997-06-18 | 1999-12-14 | Eastman Chemical Company | Polyester containing benzylidene having reduced fluorescence |
| US6368724B1 (en) | 1999-12-13 | 2002-04-09 | Eastman Chemical Company | Copolyester containing isophthalic acid, 1,4-cyclohexanedimethanol and an ultraviolet light absorbing compound and articles made therefrom |
| US6218450B1 (en) | 1999-12-13 | 2001-04-17 | Eastman Chemical Company | Copolyester containing isophthalic acid, 1,4-cyclohexanedimethanol, 4,4′-biphenyldicarboxylic acid and an ultraviolet light absorbing compound and articles made therefrom |
| US6352783B1 (en) | 1999-12-13 | 2002-03-05 | Eastman Kodak Company | Copolyester containing 4,4'-biphenyldicarboxylic acid, 1,4-cyclohexanedimethanol and an ultraviolet light absorbing compound and articles made therefrom |
-
1978
- 1978-10-12 CA CA313,211A patent/CA1096534A/en not_active Expired
- 1978-12-12 JP JP15359878A patent/JPS5488954A/en active Pending
- 1978-12-12 GB GB7848095A patent/GB2009768B/en not_active Expired
- 1978-12-12 DE DE19782853631 patent/DE2853631A1/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5709929A (en) * | 1992-10-26 | 1998-01-20 | Axxis N.V. | Plastic sheet, a process for the manufacture thereof and formed articles containing the sheet |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2009768A (en) | 1979-06-20 |
| DE2853631A1 (en) | 1979-06-13 |
| GB2009768B (en) | 1982-04-21 |
| JPS5488954A (en) | 1979-07-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |