CA2537062A1 - Manufacturing process for liquid crystalline polymer - Google Patents
Manufacturing process for liquid crystalline polymer Download PDFInfo
- Publication number
- CA2537062A1 CA2537062A1 CA 2537062 CA2537062A CA2537062A1 CA 2537062 A1 CA2537062 A1 CA 2537062A1 CA 2537062 CA2537062 CA 2537062 CA 2537062 A CA2537062 A CA 2537062A CA 2537062 A1 CA2537062 A1 CA 2537062A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- recited
- liquid crystalline
- crystalline polymer
- dicarboxylic 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.)
- Abandoned
Links
- 229920000106 Liquid crystal polymer Polymers 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 36
- 150000002009 diols Chemical class 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 22
- -1 aliphatic diesters Chemical class 0.000 claims description 19
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 13
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 12
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 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 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 claims description 4
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 150000004684 trihydrates Chemical class 0.000 claims description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 3
- 229940106691 bisphenol a Drugs 0.000 claims description 3
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 claims description 3
- UFMBOFGKHIXOTA-UHFFFAOYSA-N 2-methylterephthalic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C(O)=O UFMBOFGKHIXOTA-UHFFFAOYSA-N 0.000 claims description 2
- KWUPBWNLCARUJV-UHFFFAOYSA-N 2-tert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(O)=CC=C1C(O)=O KWUPBWNLCARUJV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 abstract description 9
- 238000000465 moulding Methods 0.000 abstract description 5
- 239000011347 resin Substances 0.000 abstract description 3
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000000155 melt Substances 0.000 description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 101000596046 Homo sapiens Plastin-2 Proteins 0.000 description 3
- 101000762938 Homo sapiens TOX high mobility group box family member 4 Proteins 0.000 description 3
- 102100026749 TOX high mobility group box family member 4 Human genes 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 101001090688 Homo sapiens Lymphocyte cytosolic protein 2 Proteins 0.000 description 2
- 102100034709 Lymphocyte cytosolic protein 2 Human genes 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- UOCIZHQMWNPGEN-UHFFFAOYSA-N dialuminum;oxygen(2-);trihydrate Chemical compound O.O.O.[O-2].[O-2].[O-2].[Al+3].[Al+3] UOCIZHQMWNPGEN-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000010998 test method Methods 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
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/916—Dicarboxylic acids and dihydroxy 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
- C08G63/78—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
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy 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
- C08G63/91—Polymers modified by chemical after-treatment
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
- C08G63/605—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds the hydroxy and carboxylic groups being bound to aromatic rings
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)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50008703P | 2003-09-04 | 2003-09-04 | |
| US60/500,087 | 2003-09-04 | ||
| US53753904P | 2004-01-20 | 2004-01-20 | |
| US60/537,539 | 2004-01-20 | ||
| PCT/US2004/028919 WO2005035619A2 (en) | 2003-09-04 | 2004-09-03 | Manufacturing process for liquid crystalline polymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2537062A1 true CA2537062A1 (en) | 2005-04-21 |
Family
ID=34437258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2537062 Abandoned CA2537062A1 (en) | 2003-09-04 | 2004-09-03 | Manufacturing process for liquid crystalline polymer |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8697817B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1660555B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4700613B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR20060085237A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2537062A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE602004012421T2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2005035619A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050261410A1 (en) * | 2004-05-21 | 2005-11-24 | Waggoner Marion G | Process for lowering the melt viscosity of polyesters |
| US9168384B2 (en) | 2011-05-23 | 2015-10-27 | Medtronic, Inc. | Electrode structure for implantable medical device |
| WO2013032974A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Solid-state polymerization of a liquid crystalline polymer |
| JP2014529627A (ja) | 2011-08-29 | 2014-11-13 | ティコナ・エルエルシー | 芳香族アミド化合物 |
| TWI554594B (zh) | 2011-08-29 | 2016-10-21 | 堤康那責任有限公司 | 高流量液晶聚合物組合物 |
| JP2014525499A (ja) | 2011-08-29 | 2014-09-29 | ティコナ・エルエルシー | 低い融解温度をもつ耐熱性液晶ポリマー組成物 |
| WO2013032967A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Cast molded parts formed form a liquid crystalline polymer |
| US8852730B2 (en) | 2011-08-29 | 2014-10-07 | Ticona Llc | Melt-extruded substrate for use in thermoformed articles |
| WO2013032975A1 (en) | 2011-08-29 | 2013-03-07 | Ticona Llc | Thermotropic liquid crystalline polymer with improved low shear viscosity |
| KR20140059825A (ko) | 2011-08-29 | 2014-05-16 | 티코나 엘엘씨 | 고유동성 액정 중합체 조성물 |
| TW201319118A (zh) | 2011-08-29 | 2013-05-16 | Ticona Llc | 低熔融黏度液晶聚合物之熔融聚合 |
| KR101996106B1 (ko) | 2011-11-15 | 2019-07-03 | 티코나 엘엘씨 | 치수 공차가 작은 성형 부품에 사용하기 위한 저-나프텐 액정 중합체 조성물 |
| US8906259B2 (en) | 2011-11-15 | 2014-12-09 | Ticona Llc | Naphthenic-rich liquid crystalline polymer composition with improved flammability performance |
| US8932483B2 (en) | 2011-11-15 | 2015-01-13 | Ticona Llc | Low naphthenic liquid crystalline polymer composition |
| KR102098411B1 (ko) | 2011-11-15 | 2020-04-07 | 티코나 엘엘씨 | 콤팩트 카메라 모듈 |
| TWI577092B (zh) | 2011-11-15 | 2017-04-01 | 堤康那責任有限公司 | 微間距電連接器及用於其中之熱塑性組合物 |
| US20130123420A1 (en) * | 2011-11-15 | 2013-05-16 | Ticona Llc | Liquid Crystalline Polymer Composition for High Voltage Electronic Components |
| KR102246137B1 (ko) * | 2012-10-16 | 2021-04-28 | 티코나 엘엘씨 | 대전방지성 액체 결정질 중합체 조성물 |
| KR102230002B1 (ko) * | 2013-03-13 | 2021-03-19 | 티코나 엘엘씨 | 컴팩트 카메라 모듈 |
| WO2014197659A1 (en) | 2013-06-07 | 2014-12-11 | Ticona Llc | High strength thermotropic liquid crystalline polymer |
| AU2015315651A1 (en) | 2014-09-12 | 2017-02-16 | E. I. Du Pont De Nemours And Company | Generation of site-specific-integration sites for complex trait loci in corn and soybean, and methods of use |
| WO2017079026A1 (en) | 2015-11-06 | 2017-05-11 | E. I. Du Pont De Nemours And Company | Generation of complex trait loci in soybean and methods of use |
| WO2017087438A1 (en) * | 2015-11-20 | 2017-05-26 | Ticona Llc | High flow polyaryletherketone composition |
| US10968347B2 (en) * | 2016-12-01 | 2021-04-06 | Jxtg Nippon Oil & Energy Corporation | Wholly aromatic liquid crystalline polyester resin |
| EP4111834A4 (en) | 2020-02-26 | 2024-06-05 | Ticona LLC | Circuit structure |
| KR20220147110A (ko) | 2020-02-26 | 2022-11-02 | 티코나 엘엘씨 | 전자 디바이스를 위한 중합체 조성물 |
| KR20220146567A (ko) | 2020-02-26 | 2022-11-01 | 티코나 엘엘씨 | 전자 디바이스 |
| US11728065B2 (en) | 2020-07-28 | 2023-08-15 | Ticona Llc | Molded interconnect device |
| US12247116B2 (en) | 2021-12-01 | 2025-03-11 | Ticona Llc | Antenna module |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4720424A (en) | 1984-06-18 | 1988-01-19 | Hoebbst Celanese Corporation | Electronic component encapsulated with a composition comprising a polymer which is capable of forming an anisotropic melt phase and substantially incapable of further chain growth upon heating |
| US4746566A (en) * | 1987-05-06 | 1988-05-24 | E. I. Dupont De Nemours And Company | Optically anisotropic melt forming aromatic copolyesters based on t-butyl-4-hydroxybenzoic acid |
| DE3721256A1 (de) | 1987-06-27 | 1989-01-12 | Akzo Gmbh | In der schmelze verarbeitbare thermotrope voll-aromatische polyester |
| KR900701932A (ko) * | 1988-10-11 | 1990-12-05 | 원본미기재 | 하이드로퀴논 폴리(이소-테레프탈레이트)p-하이드록시벤조산 중합체의 액정 중합체와 옥시비스벤젠 및 나프탈렌 유도체를 함유하는 다른 액정 중합체와의 블렌드 |
| JPH0749507B2 (ja) * | 1990-06-14 | 1995-05-31 | 積水化学工業株式会社 | ポリエステル組成物 |
| US5110896A (en) * | 1990-12-10 | 1992-05-05 | E. I. Du Pont De Nemours And Company | Thermotropic liquid crystalline polyester compositions |
| EP0705293B1 (en) | 1993-05-14 | 1998-03-18 | E.I. Du Pont De Nemours And Company | Liquid crystalline polymer compositions |
| EP0688812A1 (en) | 1994-06-20 | 1995-12-27 | Hoechst Celanese Corporation | High barrier transparent films |
| US5798432A (en) | 1996-03-22 | 1998-08-25 | Hoechst Celanese Corp. | Method of making thermotropic liquid crystalline polymers containing hydroquinone |
| JP3797444B2 (ja) * | 1996-05-24 | 2006-07-19 | 大日本インキ化学工業株式会社 | 乳酸系ポリエステル組成物及びその成形物 |
| US6294618B1 (en) * | 1998-04-09 | 2001-09-25 | E. I. Du Pont De Nemours And Company | Low viscosity liquid crystalline polymer compositions |
| US5969083A (en) * | 1998-09-18 | 1999-10-19 | Eastman Chemical Company | Liquid crystalline polyesters having a surprisingly good combination of a low melting point, a high heat distortion temperature, a low melt viscosity, and a high tensile elongation |
| JP2000143947A (ja) * | 1998-11-05 | 2000-05-26 | Toray Ind Inc | 液晶性ポリエステル樹脂組成物およびその射出成形品 |
-
2004
- 2004-09-02 US US10/934,160 patent/US8697817B2/en active Active
- 2004-09-03 WO PCT/US2004/028919 patent/WO2005035619A2/en not_active Ceased
- 2004-09-03 JP JP2006525491A patent/JP4700613B2/ja not_active Expired - Lifetime
- 2004-09-03 EP EP04809677A patent/EP1660555B1/en not_active Expired - Lifetime
- 2004-09-03 CA CA 2537062 patent/CA2537062A1/en not_active Abandoned
- 2004-09-03 KR KR20067004414A patent/KR20060085237A/ko not_active Withdrawn
- 2004-09-03 DE DE200460012421 patent/DE602004012421T2/de not_active Expired - Lifetime
-
2014
- 2014-04-11 US US14/250,423 patent/US9018315B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060085237A (ko) | 2006-07-26 |
| JP4700613B2 (ja) | 2011-06-15 |
| EP1660555A2 (en) | 2006-05-31 |
| US8697817B2 (en) | 2014-04-15 |
| US20140243481A1 (en) | 2014-08-28 |
| EP1660555B1 (en) | 2008-03-12 |
| US9018315B2 (en) | 2015-04-28 |
| DE602004012421T2 (de) | 2009-04-02 |
| WO2005035619A3 (en) | 2005-09-22 |
| US20090275697A1 (en) | 2009-11-05 |
| JP2007504327A (ja) | 2007-03-01 |
| DE602004012421D1 (de) | 2008-04-24 |
| WO2005035619A2 (en) | 2005-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140307 |