US20090111966A1 - Copolymer and method for manufacturing the same and packaging material utilizing the same - Google Patents
Copolymer and method for manufacturing the same and packaging material utilizing the same Download PDFInfo
- Publication number
- US20090111966A1 US20090111966A1 US12/049,427 US4942708A US2009111966A1 US 20090111966 A1 US20090111966 A1 US 20090111966A1 US 4942708 A US4942708 A US 4942708A US 2009111966 A1 US2009111966 A1 US 2009111966A1
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- Prior art keywords
- copolymer
- naphthalene
- cyclohexylene dimethylene
- phenyl
- combination
- 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.)
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- 0 CO[2*]OC(=O)[1*]C(C)=O Chemical compound CO[2*]OC(=O)[1*]C(C)=O 0.000 description 7
- RLSTZYJUIJWGOJ-UHFFFAOYSA-N CC(C)(C)C(NC(ONNOC(C)(C)C)=O)=O Chemical compound CC(C)(C)C(NC(ONNOC(C)(C)C)=O)=O RLSTZYJUIJWGOJ-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
- 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
Definitions
- the invention relates to a copolymer, and in particular to a packaging material utilizing the same and monomers thereof.
- packaging materials are fairly important.
- the packaging material used in light-emitting diodes should have several properties such as transparency, thermal resistance, crystallinity, and impact resistance.
- Polyester is widely used as a packaging material, but still possesses some shortcomings.
- poly ethylene terephthalate hereinafter PET
- PET has a T g of about 70° C., such that the PET does not meet requirements of high thermal resistance (Tg>100° C.) in LED packaging material.
- PEN poly(ethylene 2,6-naphthalate)
- the PEN has higher crystallinity than PET and the T g of PEN achieves 108° C., thereby effectively enhancing the thermal resistance of the packaging material utilizing the same.
- the PEN forms crystalline easily due to its high crystallinity, therefore reducing transparency and being unfavorable to form a molten state using injection packaging.
- some related arts blend the previously described two polymers and combine the easier processed, PET and the thermal resistant, PEN.
- the invention provides a copolymer, having a general formula:
- R 1 is a combination of naphthalene, phenyl, butyl, and hexyl
- R 2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl
- n is 1500 to 3000.
- the invention also provides a method for forming a copolymer, comprising: providing a diol combination of cyclohexylene dimethanol, ethylene glycol, 2-methyl-1,3-propylene glycol, and neopentylene glycol; providing a diacid combination of naphthalene dicarboxylic acid, phenyl dicarboxylic acid, succinic acid, and adipic acid; and mixing and heating the diol combination and the diacid to process condensation polymerization to form the copolymer having a general formula:
- R 1 is a combination of naphthalene, phenyl, butyl, and hexyl
- R 2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl
- n is 1500 to 3000.
- the copolymer of the invention has a general formula as:
- R 1 is a combination of naphthalene, phenyl, butyl, and hexyl.
- R 2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl.
- n is 1500 to 3000.
- the phenyl can be 1,2-phenyl, 1,3-phenyl, 1,4-phenyl, or combinations thereof
- the naphthalene can be 1,4-naphthalene, 2,3-naphthalene, 2,6-naphthalene, or combinations thereof.
- other phenyl and naphthalene substitute positions can be functional groups such as alkyl or halogen.
- the described phenyl or naphthalene comes from benzene dicarboxylic acid and naphthalene dicarboxylic acid, respectively. After condensation, the ester position is determined by the acid position substituted on the benzene and/or naphthalene.
- the crystallinity of the copolymer will be too high and transparency thereof is reduced.
- part of the ethylene is replaced with cyclohexylene dimethylene, 2-methylpropylene, and neopentylene to break the crystallinity, thereby enhancing the transparency of the copolymer.
- part of the phenyl and naphthalene can be replaced with butyl and hexyl.
- the molar ratio of cyclohexylene dimethylene, 2-methylpropylene, neopentylene, and ethylene can be tuned according to the molar ratio of naphthalene, phenyl, butyl, and hexyl. If naphthalene has higher molar ratio, the high crystallinity will reduce the transparency. If naphthalene has a lower molar ratio, the requirement of high thermal resistance will not be met.
- the described cyclohexylene dimethylene can be cis-1,2-cyclohexylene dimethylene, trans-1,2-cyclohexylene dimethylene, cis-1,3-cyclohexylene dimethylene, trans-1,3-cyclohexylene dimethylene, cis-1,4-cyclohexylene dimethylene, trans-1,4-cyclohexylene dimethylene, or combinations thereof.
- the described cyclohexylene dimethylene comes from cyclohexylene dimethanol, the ethylene comes from ethylene glycol, respectively. After condensation, the ester position is determined by the methanol position substituted on the cyclohexane. It is understood that the copolymer crystallinity depends on the steric structure. Accordingly, tuning the acid/alcohol substitution position may modify the thermal resistance and transparency of the copolymer in embodiments of the invention.
- the invention also provides a method for forming the described copolymer.
- the diol combination is a combination of cyclohexylene dimethanol, ethylene glycol, 2-methyl-1,3-propylene glycol, and neopentylene glycol.
- the diacid combination is a combination of naphthalene dicarboxylic acid, benzene dicarboxylic acid, succinic acid, and adipic acid.
- a mixture of the diol combination and the diacid combination is heated to process condensation polymerization to form the copolymer.
- the copolymer has the general formula:
- R 1 is a combination of naphthalene, phenyl, butyl, and hexyl.
- R 2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl.
- n is 1500 to 3000.
- the phenyl can be 1,2-phenyl, 1,3-phenyl, 1,4-phenyl, or combinations thereof
- the naphthalene can be 1,4-naphthalene, 2,3-naphthalene, 2,6-naphthalene, or combinations thereof
- the cyclohexylene dimethylene can be cis-1,2-cyclohexylene dimethylene, trans-1,2-cyclohexylene dimethylene, cis-1,3-cyclohexylene dimethylene, trans-1,3-cyclohexylene dimethylene, cis-1,4-cyclohexylene dimethylene, trans-1,4-cyclohexylene dimethylene, or combinations thereof.
- the described copolymer is injection molded to package a light-emitting device such as LED.
- the described copolymer has a transparency greater than 80%, a thermal resistance greater than 100° C., a moisture absorption less than 0.5 wt %, and a yellowing resistance under UV and/or climate greater than 1000 hours.
- NDC 2,6-naphthalene dicarboxylic acid
- 1,4-benzene dicarboxylic acid were weighted according to an appropriate molar ratio to be served as a diacid combination.
- Cis/trans 1,4-cyclohexylene dimethanol (hereinafter CHDM) and ethylene glycol were weighted according to an appropriate molar ratio to be served as a diol combination thereof.
- CHDM Cis/trans 1,4-cyclohexylene dimethanol
- ethylene glycol were weighted according to an appropriate molar ratio to be served as a diol combination thereof.
- the diacid combination and the diol combination were charged in a round bottom bottle, heated to 240-290° C. and then vacuumed for processing condensation polymerization to yield a copolymer.
- the copolymer properties such as inherent viscosity, Tg, transparency, and yellowing resistance were measured.
- the monomer molar ratio and the copolymer properties were tabulated
- T ch means the temperature of crystallization measured while heating from the solid state
- T cc means the temperature of crystallization measured while cooling from the melt
- T m means the crystalline melting temperature.
- the copolymers introduced by 2-methyl-1,3-propylene glycol, neopentylene glycol, succinic acid, and adipic acid were amorphous.
- the copolymer transparency was therefore enhanced and the back-end processing of the injection molding is improved.
Abstract
The disclosed is a copolymer having a formula as:
R1 is a combination of naphthalene, phenylene, butyl, and hexyl. R2 is a combination of ethylene, cyclohexene, 2-methylpropyl, and neopentyl. n is a number of 1500 to 3000. The copolymer has a transparency greater than 80%, a thermal resistance greater than 100° C., a moisture absorption less than 0.5 wt %, and yellowing under UV/climate resistance greater than 1000 hours, such that the copolymer is adapted to be applied in packaging material for light emitting devices.
Description
- 1. Field of the Invention
- The invention relates to a copolymer, and in particular to a packaging material utilizing the same and monomers thereof.
- 2. Description of the Related Art
- For light-emitting devices, packaging materials are fairly important. For example, the packaging material used in light-emitting diodes (hereinafter LED) should have several properties such as transparency, thermal resistance, crystallinity, and impact resistance. Polyester is widely used as a packaging material, but still possesses some shortcomings. For instance, poly ethylene terephthalate (hereinafter PET) has a Tg of about 70° C., such that the PET does not meet requirements of high thermal resistance (Tg>100° C.) in LED packaging material. Some related arts replace the monomer terephthalic acid, so-called 1,4-benzenedicarboxylic acid, with 2,6-naphthalenedicarboxylic acid to form poly(ethylene 2,6-naphthalate) (hereinafter PEN) to solve the described problem. The PEN has higher crystallinity than PET and the Tg of PEN achieves 108° C., thereby effectively enhancing the thermal resistance of the packaging material utilizing the same. However, the PEN forms crystalline easily due to its high crystallinity, therefore reducing transparency and being unfavorable to form a molten state using injection packaging. Meanwhile, some related arts blend the previously described two polymers and combine the easier processed, PET and the thermal resistant, PEN. Nevertheless, because the blend standard is not unified and blend properties is easily influenced by polymerizing degree or molar ratio of PET and/or PEN, practical application of the blend confront difficulties such as reproduction and magnification. Thus, designing a novel polymer structure is called for, to combine the advantages of PET and PEN and standardizing packaging material properties.
- The invention provides a copolymer, having a general formula:
- wherein R1 is a combination of naphthalene, phenyl, butyl, and hexyl, R2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl, and n is 1500 to 3000.
- The invention also provides a method for forming a copolymer, comprising: providing a diol combination of cyclohexylene dimethanol, ethylene glycol, 2-methyl-1,3-propylene glycol, and neopentylene glycol; providing a diacid combination of naphthalene dicarboxylic acid, phenyl dicarboxylic acid, succinic acid, and adipic acid; and mixing and heating the diol combination and the diacid to process condensation polymerization to form the copolymer having a general formula:
- wherein R1 is a combination of naphthalene, phenyl, butyl, and hexyl, R2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl, and n is 1500 to 3000.
- A detailed description is given in the following embodiments.
- The following description is of the best-contemplated mode of carrying out the invention. This description is made for the purpose of illustrating the general principles of the invention and should not be taken in a limiting sense. The scope of the invention is best determined by reference to the appended claims.
- Shortcomings such as insufficient thermal resistance of PET and inadequate transparency of PEN can be improved by the copolymer of the invention. The copolymer of the invention has a general formula as:
- R1 is a combination of naphthalene, phenyl, butyl, and hexyl. R2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl. n is 1500 to 3000. The phenyl can be 1,2-phenyl, 1,3-phenyl, 1,4-phenyl, or combinations thereof, the naphthalene can be 1,4-naphthalene, 2,3-naphthalene, 2,6-naphthalene, or combinations thereof. Under the condition that esterification condensation is not influenced, other phenyl and naphthalene substitute positions can be functional groups such as alkyl or halogen. The described phenyl or naphthalene comes from benzene dicarboxylic acid and naphthalene dicarboxylic acid, respectively. After condensation, the ester position is determined by the acid position substituted on the benzene and/or naphthalene.
- If the molar ratio of the naphthalene in R1 is higher than 90%, the crystallinity of the copolymer will be too high and transparency thereof is reduced. For improving transparency, part of the ethylene is replaced with cyclohexylene dimethylene, 2-methylpropylene, and neopentylene to break the crystallinity, thereby enhancing the transparency of the copolymer. On the basis of the described reason, part of the phenyl and naphthalene can be replaced with butyl and hexyl.
- The molar ratio of cyclohexylene dimethylene, 2-methylpropylene, neopentylene, and ethylene can be tuned according to the molar ratio of naphthalene, phenyl, butyl, and hexyl. If naphthalene has higher molar ratio, the high crystallinity will reduce the transparency. If naphthalene has a lower molar ratio, the requirement of high thermal resistance will not be met.
- The described cyclohexylene dimethylene can be cis-1,2-cyclohexylene dimethylene, trans-1,2-cyclohexylene dimethylene, cis-1,3-cyclohexylene dimethylene, trans-1,3-cyclohexylene dimethylene, cis-1,4-cyclohexylene dimethylene, trans-1,4-cyclohexylene dimethylene, or combinations thereof. The described cyclohexylene dimethylene comes from cyclohexylene dimethanol, the ethylene comes from ethylene glycol, respectively. After condensation, the ester position is determined by the methanol position substituted on the cyclohexane. It is understood that the copolymer crystallinity depends on the steric structure. Accordingly, tuning the acid/alcohol substitution position may modify the thermal resistance and transparency of the copolymer in embodiments of the invention.
- The invention also provides a method for forming the described copolymer. First, providing a diol combination and a diacid combination, and these two combinations have same molar ratio. The diol combination is a combination of cyclohexylene dimethanol, ethylene glycol, 2-methyl-1,3-propylene glycol, and neopentylene glycol. The diacid combination is a combination of naphthalene dicarboxylic acid, benzene dicarboxylic acid, succinic acid, and adipic acid. Subsequently, a mixture of the diol combination and the diacid combination is heated to process condensation polymerization to form the copolymer. The copolymer has the general formula:
- R1 is a combination of naphthalene, phenyl, butyl, and hexyl. R2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl. n is 1500 to 3000. As described above, the phenyl can be 1,2-phenyl, 1,3-phenyl, 1,4-phenyl, or combinations thereof, the naphthalene can be 1,4-naphthalene, 2,3-naphthalene, 2,6-naphthalene, or combinations thereof, and the cyclohexylene dimethylene can be cis-1,2-cyclohexylene dimethylene, trans-1,2-cyclohexylene dimethylene, cis-1,3-cyclohexylene dimethylene, trans-1,3-cyclohexylene dimethylene, cis-1,4-cyclohexylene dimethylene, trans-1,4-cyclohexylene dimethylene, or combinations thereof.
- In one embodiment of the invention, the described copolymer is injection molded to package a light-emitting device such as LED. The described copolymer has a transparency greater than 80%, a thermal resistance greater than 100° C., a moisture absorption less than 0.5 wt %, and a yellowing resistance under UV and/or climate greater than 1000 hours.
- 2,6-naphthalene dicarboxylic acid (hereinafter NDC) and 1,4-benzene dicarboxylic acid were weighted according to an appropriate molar ratio to be served as a diacid combination. Cis/trans 1,4-cyclohexylene dimethanol (hereinafter CHDM) and ethylene glycol were weighted according to an appropriate molar ratio to be served as a diol combination thereof. The diacid combination and the diol combination were charged in a round bottom bottle, heated to 240-290° C. and then vacuumed for processing condensation polymerization to yield a copolymer. The copolymer properties such as inherent viscosity, Tg, transparency, and yellowing resistance were measured. The monomer molar ratio and the copolymer properties were tabulated as in Table 1.
-
TABLE 1 NDC content 36 51 51 58 0 73 80 87 94 100 (mol %) CHDM 30 30 70 80 100 30 30 30 30 30 content (mol %) Inherent 0.62 0.57 0.58 0.60 0.63 0.63 0.60 0.51 0.42 037 viscosity Tg (° C.) 93.78 96.57 97.28 97.28 84.61 105 106.68 108.0 108.47 108.74 Transparency 86 85 85 84 88 84 84 83 83 83 (%) Yellowing 1000 1000 1500 1500 2000 1000 1000 1000 1000 1000 resistance under UV (hour) - Referring to Table 1, all of the copolymers of the invention have transparencies greater than 80% and yellowing resistance under UV and/or climate greater than 1000 hours.
- In this Example, the molar ratio of CHDM and ethylene glycol is tuned to measure the copolymer properties.
-
TABLE 2 Product No. PET-C-1 PET-C-2 PET-C-3 PET-C-4 PET-C-5 PET-C-6 CHDM (mol %) 5 10 15 20 25 30 Inherent viscosity 0.46 0.59 0.54 0.53 0.50 0.51 Tg (° C.) 77.23 76.37 73.07 73.81 77.8 77.11 Tch (° C.) 159.2 167.78 162.88 — — — Tcc (° C.) 151.09 148.01 155.9 — — — Tm (° C.) 241.42 225.99 217.51 206.07 194.9 — Note: — means the signal peak disappears. - In Table 2, Tch means the temperature of crystallization measured while heating from the solid state, Tcc means the temperature of crystallization measured while cooling from the melt, and Tm means the crystalline melting temperature. As shown in Table 2, when the molar ratio of CHDM and ethylene glycol is greater than 80:20, the copolymer is amorphous. The copolymer transparency was therefore enhanced and the back-end processing of the injection molding is improved. The disappearance of Tcc, Tch, and Tm peak means that the copolymer exhibits an amorphous state.
- In this example, part of ethylene glycol is replaced with 2-methyl-1,3-propylene glycol or neopentylene glycol, and part of 1,4-benzene dicarboxylic acid is replaced with succinic acid or adipic acid. The copolymer properties were shown as in Table 3.
-
TABLE 3 PET-2-methyl- PET- PET-apidic PET-succinic 1,3-propylene neopentylene acid acid glycol glycol Introduced Adipic acid Succinic acid 2-methyl-1,3- Neopentylene monomer propylene glycol glycol mol % 20 20 20 20 Inherent 0.54 0.62 0.59 0.65 viscosity Tg (° C.) 53.5 60.8 62.3 71.25 Tch (° C.) — — — — Tcc (° C.) — — — — Tm (° C.) — — — — Note: means the signal peak is disappear. - As shown in Table 3, the copolymers introduced by 2-methyl-1,3-propylene glycol, neopentylene glycol, succinic acid, and adipic acid were amorphous. The copolymer transparency was therefore enhanced and the back-end processing of the injection molding is improved.
- While the invention has been described by way of example and in terms of preferred embodiment, it is to be understood that the invention is not limited thereto. To the contrary, it is intended to cover various modifications and similar arrangements (as would be apparent to those skilled in the art). Therefore, the scope of the appended claims should be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements.
Claims (13)
2. The copolymer as claimed in claim 1 , wherein the cyclohexylene dimethylene comprises cis-1,2-cyclohexylene dimethylene, trans-1,2-cyclohexylene dimethylene, cis-1,3-cyclohexylene dimethylene, trans-1,3-cyclohexylene dimethylene, cis-1,4-cyclohexylene dimethylene, trans-1,4-cyclohexylene dimethylene, or combinations thereof.
3. The copolymer as claimed in claim 1 , wherein the naphthalene comprises 1,4-naphthalene, 2,3-naphthalene, 2,6-naphthalene, or combinations thereof.
4. The copolymer as claimed in claim 1 , wherein the phenyl comprises 1,2-phenyl, 1,3-phenyl, 1,4-phenyl, or combinations thereof.
5. The copolymer as claimed in claim 1 having a transparency greater than 80%.
6. The copolymer as claimed in claim 1 having a thermal resistance greater than 100° C.
7. The copolymer as claimed in claim 1 having a moisture absorption less than 0.5 wt %.
8. The copolymer as claimed in claim 1 having a yellowing resistance under UV and/or climate greater than 1000 hours.
9. A packaging material, comprising the copolymer as claimed in claim 1 .
10. A method for forming a copolymer, comprising:
providing a diol combination of cyclohexylene dimethanol, ethylene glycol, 2-methyl-1,3-propylene glycol, and neopentylene glycol;
providing a diacid combination of naphthalene dicarboxylic acid, benzene dicarboxylic acid, succinic acid, and adipic acid; and
mixing and heating the diol combination and the diacid to process condensation polymerization to form the copolymer having a general formula:
wherein
R1 is a combination of naphthalene, phenyl, butyl, and hexyl;
R2 is a combination of cyclohexylene dimethylene, ethylene, 2-methylpropyl, and neopentyl; and
n is 1500 to 3000.
11. The method as claimed in claim 10 , wherein the cyclohexylene dimethylene comprises cis-1,2-cyclohexylene dimethylene, trans-1,2-cyclohexylene dimethylene, cis-1,3-cyclohexylene dimethylene, trans-1,3-cyclohexylene dimethylene, cis-1,4-cyclohexylene dimethylene, trans-1,4-cyclohexylene dimethylene, or combinations thereof.
12. The method as claimed in claim 1 , wherein the naphthalene comprises 1,4-naphthalene, 2,3-naphthalene, 2,6-naphthalene, or combinations thereof.
13. The method as claimed in claim 1 , wherein the phenyl comprises 1,2-phenyl, 1,3-phenyl, 1,4-phenyl, or combinations thereof.
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US12/983,541 US8389666B2 (en) | 2007-10-29 | 2011-01-03 | Copolymer and method for manufacturing the same and packaging material utilizing the same |
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TW96140578 | 2007-10-29 | ||
TW096140578A TWI368624B (en) | 2007-10-29 | 2007-10-29 | Coplymer and method for manufacturing the same and packaging material utilizing the same |
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US12/983,541 Division US8389666B2 (en) | 2007-10-29 | 2011-01-03 | Copolymer and method for manufacturing the same and packaging material utilizing the same |
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US12/049,427 Abandoned US20090111966A1 (en) | 2007-10-29 | 2008-03-17 | Copolymer and method for manufacturing the same and packaging material utilizing the same |
US12/983,541 Active 2028-06-19 US8389666B2 (en) | 2007-10-29 | 2011-01-03 | Copolymer and method for manufacturing the same and packaging material utilizing the same |
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US12/983,541 Active 2028-06-19 US8389666B2 (en) | 2007-10-29 | 2011-01-03 | Copolymer and method for manufacturing the same and packaging material utilizing the same |
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TW (1) | TWI368624B (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4742151A (en) * | 1986-06-26 | 1988-05-03 | Toyo Boseki Kabushiki Kaisha | Ultra-high-molecular-weight polyesters |
US20070059465A1 (en) * | 2004-05-20 | 2007-03-15 | Thompson David E | Polyester Resins for High-Strength Articles |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4259458A (en) * | 1979-08-09 | 1981-03-31 | Union Carbide Corporation | Polyarylate containing blends |
US4381379A (en) * | 1981-03-25 | 1983-04-26 | Daicel Chemical Industries, Ltd. | Polyester containing 2-methyl-1,3-propylene terephthalate units |
US4529458A (en) * | 1982-07-19 | 1985-07-16 | Allied Corporation | Compacted amorphous ribbon |
US4792573A (en) * | 1988-04-01 | 1988-12-20 | The Goodyear Tire & Rubber Company | Preparation of ultra-high molecular weight polyester |
US5855924A (en) * | 1995-12-27 | 1999-01-05 | Siemens Microelectronics, Inc. | Closed-mold for LED alphanumeric displays |
US5656715A (en) * | 1996-06-26 | 1997-08-12 | Eastman Chemical Company | Copolyesters based on 1,4-cyclohexanedimethanol having improved stability |
US6537470B1 (en) * | 2000-09-01 | 2003-03-25 | Honeywell International Inc. | Rapid densification of porous bodies (preforms) with high viscosity resins or pitches using a resin transfer molding process |
FR2828199A1 (en) | 2001-07-31 | 2003-02-07 | Perrier Vittel Man Technologie | Polyethylene terephthalate polyester useful for making hollow containers, e.g. bottles, has a low intrinsic viscosity and a low acetaldehyde content |
DE10153704A1 (en) * | 2001-10-31 | 2003-05-15 | Krauss Maffei Kunststofftech | Plastic injection molding machine |
CA2534352A1 (en) * | 2003-08-08 | 2005-02-17 | Arriva Pharmaceuticals, Inc. | Methods of protein production in yeast |
CN100480305C (en) | 2003-09-11 | 2009-04-22 | 帝人杜邦菲林日本株式会社 | Polyester film |
JP2006051068A (en) * | 2004-08-10 | 2006-02-23 | Sri Sports Ltd | Production method of golf ball |
-
2007
- 2007-10-29 TW TW096140578A patent/TWI368624B/en active
-
2008
- 2008-03-17 US US12/049,427 patent/US20090111966A1/en not_active Abandoned
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2011
- 2011-01-03 US US12/983,541 patent/US8389666B2/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4742151A (en) * | 1986-06-26 | 1988-05-03 | Toyo Boseki Kabushiki Kaisha | Ultra-high-molecular-weight polyesters |
US20070059465A1 (en) * | 2004-05-20 | 2007-03-15 | Thompson David E | Polyester Resins for High-Strength Articles |
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US20110098437A1 (en) | 2011-04-28 |
TWI368624B (en) | 2012-07-21 |
TW200918574A (en) | 2009-05-01 |
US8389666B2 (en) | 2013-03-05 |
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Owner name: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE, TAIWAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LIN, CHIH-HSIANG;CHUANG, YA-LAN;TSAT, PEI-JUNG;AND OTHERS;REEL/FRAME:020658/0118 Effective date: 20071205 |
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STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |