CN1298765C - Poly(ester-amide) containing isosorbide unit and process for preparing same - Google Patents
Poly(ester-amide) containing isosorbide unit and process for preparing same Download PDFInfo
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- CN1298765C CN1298765C CNB2005100798949A CN200510079894A CN1298765C CN 1298765 C CN1298765 C CN 1298765C CN B2005100798949 A CNB2005100798949 A CN B2005100798949A CN 200510079894 A CN200510079894 A CN 200510079894A CN 1298765 C CN1298765 C CN 1298765C
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- diacid chloride
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- polyesteramide
- chloride
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- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical group O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 title description 23
- 238000004519 manufacturing process Methods 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 137
- 239000000178 monomer Substances 0.000 claims abstract description 52
- 150000004985 diamines Chemical class 0.000 claims abstract description 36
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 14
- 239000002798 polar solvent Substances 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000006096 absorbing agent Substances 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 8
- 230000003287 optical effect Effects 0.000 abstract description 4
- 238000000354 decomposition reaction Methods 0.000 abstract description 3
- 239000012528 membrane Substances 0.000 abstract description 3
- 229920003023 plastic Polymers 0.000 abstract description 3
- 239000013307 optical fiber Substances 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 230000005526 G1 to G0 transition Effects 0.000 abstract 1
- 238000003754 machining Methods 0.000 abstract 1
- 229960002479 isosorbide Drugs 0.000 description 22
- 229920000728 polyester Polymers 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical group OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Landscapes
- Polyamides (AREA)
Abstract
The present invention relates to polyesteramide containing isosorbitol units and a preparation method thereof, which belongs to the technical field of macromolecular materials. The structure of the polyesteramide is disclosed in the specification. The present invention uses the preparation method that a diamine monomer containg isosorbitol and ester bonds and diacid chloride are reacted to synthesize the polyesteramide. The polyesteramide prepared by the present invention has good solubility, good film forming performance and good mechanical property, and has the advantages of good thermal stability, high decomposition temperature and convenient machining. The present invention can be used in optical plastics, CD or DVD base materials, lenses, dashboard windows or hoods, prism reflectors, thin membranes, sheet materials, or optical fiber, etc. In addition, the polyesteramide has optical activity, and can be used in chiral stationary phases, chiral separation membranes, etc.
Description
Technical field
The invention belongs to technical field of polymer materials, particularly contain polyesteramide of isoscrbierite unit and preparation method thereof.
Background technology
Isosorbide (1,4:3,6-two dehydration-D-sorbyl alcohols) as the dewatered product of sorbyl alcohol, have abundant, the special advantages such as chirality feature, degradable and Heat stability is good of raw material sources, therefore great application prospect is arranged at aspects such as liquid crystal, optical plasticss.(the CN1298343 of E. I. Du Pont de Nemours and Co, CN1298346, CN1298416, CN1298417A, CN1298426) invented a series of polyester that contain Isosorbide, this polyester utilizes the condensation reaction of aromatic diacid and glycol, producing the polyester that reduced concentration viscosity is at least 0.15dL/g-0.35dL/g,, can obtain more full-bodied polyester with itself and other thermosetting polyester blend.Because its excellent properties, this polyester can be used to optical plastics, can make CD (CD), high definition CD (DVD), CD or base material (DVD), lens, panel board window or outer cover, prism reflector, film, sheet material or optical fiber etc.Patent CN1442460A has invented a kind of coating that contains Isosorbide, this coating utilizes the chirality feature of Isosorbide, can change and variable color with viewing angle, and have good anti-ultraviolet, acid and alkali-resistance, heat-resisting and weather resistance, can be applied to the external coating of multiple material.It is nuclear that patent US20020013483A has synthesized with the Isosorbide with Isosorbide and P-hydroxybenzoic acid, the product that two ends are hydroxyl.In addition, patent US20020115817A1, US20010003359A1, WO 03/027119A1 etc. has synthesized a series of vinylformic acid list dibasic acid esters that contain Isosorbide, these esters and some are had nematic liquid crystal monomer copolymerization, can obtain to have the cross linking membrane of cholesteryl phase, can be used for color filer.
Polymeric amide has excellent heat, power performance, and good chemical stability; But common aromatic polyamide is insoluble to general organic reagent usually, adopts the vitriol oil that processing units is had relatively high expectations in the course of processing, simultaneously, to some special occasions, has limited its application.
The applicant had once proposed name and had been called that " containing diamine monomer of di-dehydrated hexitol unit and preparation method thereof ", application number are 200410080283.1, publication number is: the patent application of CN1616462A, a kind of preparation method of diamine monomer is disclosed, comprising the preparation of the diamine monomer that contains Isosorbide.
Summary of the invention
The objective of the invention is to propose polyesteramide that contains isoscrbierite unit and preparation method thereof, utilize the disclosed technology of preparing that contains the unitary diamine monomer of two dewatering hexitols of the applicant, prepare the diamine monomer that contains Isosorbide, and further preparation contains the polyesteramide of isoscrbierite unit, to overcome the weak point of existing aromatic series or semiaromatic polyamide composition, make the polymeric amide of preparation have good solubility, film forming properties and mechanical property, have also that thermal stability is good, decomposition temperature is high, and process advantage easily.
The polyesteramide that contains isoscrbierite unit that the present invention proposes, the structure of this polyesteramide is:
Employing contains the diamine monomer and the diacid chloride reaction of Isosorbide, synthetic obtaining:
In the following formula, Ar ' is:
In any,
R is any or multiple in the following structure:
n＝2～10
The above-mentioned preparation method who contains the polyesteramide of isoscrbierite unit may further comprise the steps:
(1) add polar solvent in containing the diamine monomer of isoscrbierite unit, additional proportion is: diamine monomer: polar solvent=1mol: 1L～4L;
(2) add earlier acid absorber in above-mentioned solution, add diacid chloride again, the mol ratio of adding is: diamine monomer: acid absorber: diacid chloride=1: 1: 0.9～1.1, under 0～60 ℃ and nitrogen protection, stirred 1～24 hour, and obtain the heavy-gravity polyamide solution.
Polar solvent in the aforesaid method is N, any in dinethylformamide, N,N-dimethylacetamide, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO) or the hexamethylphosphoramide.
The diacid chloride of aforesaid method is that one or more of following classes of compounds use with any mixed:
Be called for short diacid chloride C
n＝2～16
Be called for short diacid chloride D
Be called for short diacid chloride E
Be called for short diacid chloride F
Be called for short diacid chloride H
(9)
Be called for short diacid chloride K
Be called for short diacid chloride N
Be called for short diacid chloride O
(16)
Acid absorber in the aforesaid method is that in pyridine or the triethylamine one or both use with any mixed.
For can be applicable to diacid chloride composition commonly used of the present invention, be not particularly limited usually, for example aromatic series diacid chloride and aliphatics diacid chloride and comprise above-mentioned deutero-diacid chloride.These diacid chloride compositions can be by the mixture use of two or more diacid chlorides alone or in combination.
The preparation method of the polyesteramide that contains Isosorbide of proposition of the present invention, owing to introduced alicyclic structure and Isosorbide has twist structure, therefore stop tightly packed between the molecular chain, increased the free volume of material, and then improved the solvability of material.The polymeric amide that synthetic contains Isosorbide generally has good solubility, dissolves in general polar solvent, and good film forming properties is arranged, and processing is convenient, can prepare film, fiber or the like.In addition, because the thermostability of Isosorbide, the synthetic polymeric amide has high glass transition, can be greater than 200 ℃, and thermal stability is good, and decomposition temperature can be greater than 400 ℃.Diacid chloride rigidity as employing is big, then can reach higher temperature.In addition, though introduced alicyclic structure, the alicyclic of Isosorbide has certain rigid, thereby has the good mechanical performance.In a word, the polymeric amide that contains Isosorbide can be used in the fields such as opticglass, optics, chiral separation owing to its excellent performance.
Embodiment
Embodiment 1
(1) add polar solvent N in containing the diamine monomer of Isosorbide, dinethylformamide, additional proportion are 1mol: 1L;
(2) in above-mentioned solution, add the acid absorber pyridine earlier; add diacid chloride A again, the mol ratio of adding is: diamines: pyridine: diacid chloride=0.9: 0.9: 1, stirred 1 hour under ice-water bath and nitrogen protection; room temperature reaction is 4 hours again, obtains the heavy-gravity polyamide solution.
Embodiment 2
(1) add the polar solvent N,N-dimethylacetamide in containing the diamine monomer of Isosorbide, additional proportion is 1mol: 2L;
(2) add the acid absorber pyridine earlier in above-mentioned solution, add diacid chloride B again, the mol ratio of adding is: diamines: pyridine: diacid chloride=1: 1: 1, under room temperature and nitrogen protection, stirred 1 hour, and obtain the heavy-gravity polyamide solution.
Embodiment 3
(1) add the polar solvent dimethyl sulfoxide (DMSO) in containing the diamine monomer of Isosorbide, additional proportion is 1mol: 3L;
(2) add earlier the acid absorber pyridine in above-mentioned solution, add diacid chloride C again, the mol ratio of adding is: diamines: pyridine: diacid chloride=1.1: 1.1: 1, under 60 ℃ and nitrogen protection, stirred 8 hours, and obtain the heavy-gravity polyamide solution.
Embodiment 4
(1) add the polar solvent N-Methyl pyrrolidone in the diamine monomer that contains Isosorbide of above-mentioned preparation, additional proportion is 1mol: 4L;
(2) add the acid absorber triethylamine earlier in above-mentioned solution, add diacid chloride D again, the mol ratio of adding is: diamines: triethylamine: diacid chloride=1.05: 1.05: 1, under room temperature and nitrogen protection, stirred 16 hours, and obtain the heavy-gravity polyamide solution.
Embodiment 5
(1) add the polar solvent N-Methyl pyrrolidone in containing the diamine monomer of Isosorbide, additional proportion is 1mol: 3L;
(2) add the acid absorber triethylamine earlier in above-mentioned solution, add diacid chloride E again, the mol ratio of adding is: diamines: triethylamine: diacid chloride=0.95: 0.95: 1, under room temperature and nitrogen protection, stirred 24 hours, and obtain the heavy-gravity polyamide solution.
Embodiment 6
(1) add the polar solvent hexamethylphosphoramide in containing the diamine monomer of Isosorbide, additional proportion is 1mol: 2L;
(2) in above-mentioned solution, add acid absorber triethylamine and pyridine earlier; add diacid chloride F again; the mol ratio that adds is: diamines: triethylamine: pyridine: diacid chloride=1.02: 0.51: 0.51: 1, under room temperature and nitrogen protection, stirred 18 hours, and obtain the heavy-gravity polyamide solution.
Embodiment 7: the diacid chloride monomer adopts diacid chloride G, and other technology is identical with embodiment 1.
Embodiment 8: the diacid chloride monomer adopts diacid chloride H, and other technology is identical with embodiment 1.
Embodiment 9: the diacid chloride monomer adopts diacid chloride I, and other technology is identical with embodiment 1.
Embodiment 10: the diacid chloride monomer adopts diacid chloride J, and other technology is identical with embodiment 1.
Embodiment 11: the diacid chloride monomer adopts diacid chloride K, and other technology is identical with embodiment 1.
Embodiment 12: the diacid chloride monomer adopts diacid chloride L, and other technology is identical with embodiment 3.
Embodiment 13: the diacid chloride monomer adopts diacid chloride M, and other technology is identical with embodiment 3.
Embodiment 14: the diacid chloride monomer adopts diacid chloride N, and other technology is identical with embodiment 2.
Embodiment 15: the diacid chloride monomer adopts diacid chloride O, and other technology is identical with embodiment 2.
Embodiment 16: the diacid chloride monomer adopts diacid chloride P, and other technology is identical with embodiment 2.
Embodiment 17: the diacid chloride monomer adopts diacid chloride P and diacid chloride E, and diacid chloride P: diacid chloride E: diamine monomer=0.5: 0.5: 1, other technology is identical with embodiment 2.
Embodiment 18: the diacid chloride monomer adopts diacid chloride B and diacid chloride D, and diacid chloride B: diacid chloride D: diamine monomer=0.1: 0.9: 1, other technology is identical with embodiment 2.
Embodiment 19: the diacid chloride monomer adopts diacid chloride B and diacid chloride D, and diacid chloride B: diacid chloride D: diamine monomer=0.8: 0.2: 1, other technology is identical with embodiment 2.
Embodiment 20: the diacid chloride monomer adopts diacid chloride D and diacid chloride M, and diacid chloride D: diacid chloride M: diamine monomer=0.2: 0.8: 1, other technology is identical with embodiment 4.
Embodiment 21: the diacid chloride monomer adopts diacid chloride D and diacid chloride M, and diacid chloride D: diacid chloride M: diamine monomer=0.4: 0.6: 1, other technology is identical with embodiment 4.
Embodiment 22: the diacid chloride monomer adopts diacid chloride D and diacid chloride I, and diacid chloride D: diacid chloride I: diamine monomer=0.1: 0.9: 1, other technology is identical with embodiment 5.
Embodiment 23: the diacid chloride monomer adopts diacid chloride K and diacid chloride I, and diacid chloride K: diacid chloride I: diamine monomer=0.9: 0.1: 1, other technology is identical with embodiment 5.
Embodiment 24: the diacid chloride monomer adopts diacid chloride K and diacid chloride I, and diacid chloride K: diacid chloride I: diamine monomer=0.4: 0.6: 1, other technology is identical with embodiment 5.
Embodiment 25: the diacid chloride monomer adopts diacid chloride J and diacid chloride D, and diacid chloride J: diacid chloride D: diamine monomer=0.4: 0.6: 1, other technology is identical with embodiment 5.
Embodiment 26: the diacid chloride monomer adopts diacid chloride J, diacid chloride B and diacid chloride D, and diacid chloride J: diacid chloride B: diacid chloride D: diamine monomer=0.4: 0.4: 0.2: 1, other technology is identical with embodiment 5.
Embodiment 27: the diacid chloride monomer adopts diacid chloride J, diacid chloride B and diacid chloride D, and diacid chloride J: diacid chloride B: diacid chloride D: diamine monomer=0.5: 0.2: 0.3: 1, other technology is identical with embodiment 5.
Claims (5)
1, a kind of polyesteramide that contains isoscrbierite unit is characterized in that the structure of this polyesteramide is:
In the following formula, Ar ' is:
Or
In any,
R is any or multiple in the following structure:
n＝2～10
R '=-CH3 or
Or
2, a kind ofly prepare the method that contains the polyesteramide of isoscrbierite unit as claimed in claim 1, it is characterized in that this preparation method may further comprise the steps:
(1) add polar solvent in containing the diamine monomer of isoscrbierite unit, additional proportion is: diamine monomer: polar solvent=1mol: 1L～4L;
(2) add earlier acid absorber in above-mentioned solution, add diacid chloride again, the mol ratio of adding is: diamine monomer: acid absorber: diacid chloride=1: 1: 0.9～1.1, under 0～60 ℃ and nitrogen protection, stirred 1～24 hour, and obtain the heavy-gravity polyamide solution.
3, method as claimed in claim 2 is characterized in that, described polar solvent is N, any in dinethylformamide, N,N-dimethylacetamide, N-Methyl pyrrolidone, dimethyl sulfoxide (DMSO) or the hexamethylphosphoramide.
4, method as claimed in claim 2 is characterized in that, described diacid chloride is that one or more of following classes of compounds use with any mixed:
Be called for short diacid chloride B
Be called for short diacid chloride C
Diacid chloride E is called for short in n=2～16
R=-CH3 or
Be called for short diacid chloride F
Be called for short diacid chloride H
(9)
Be called for short diacid chloride I
Be called for short diacid chloride J
Be called for short diacid chloride M
Be called for short diacid chloride N
Be called for short diacid chloride O
(16)
Be called for short diacid chloride P
5, method as claimed in claim 2 is characterized in that wherein said acid absorber is that in pyridine or the triethylamine one or both use with any mixed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100798949A CN1298765C (en) | 2005-07-01 | 2005-07-01 | Poly(ester-amide) containing isosorbide unit and process for preparing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100798949A CN1298765C (en) | 2005-07-01 | 2005-07-01 | Poly(ester-amide) containing isosorbide unit and process for preparing same |
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| CN1702096A CN1702096A (en) | 2005-11-30 |
| CN1298765C true CN1298765C (en) | 2007-02-07 |
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| CNB2005100798949A Expired - Fee Related CN1298765C (en) | 2005-07-01 | 2005-07-01 | Poly(ester-amide) containing isosorbide unit and process for preparing same |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101648958B (en) * | 2009-09-15 | 2011-11-16 | 清华大学 | Preparation method of dianhydride monomer containing chiral dianhydro-hexitol |
| CN110911642B (en) * | 2018-09-14 | 2021-05-11 | 多氟多化工股份有限公司 | Binder for pole piece, preparation method of binder, silicon-based pole piece and lithium ion battery |
| CN111019126B (en) * | 2019-12-06 | 2022-04-15 | 苏州大学 | Polyester amide and preparation method thereof |
| CN116004028B (en) * | 2022-12-28 | 2024-07-02 | 江苏丽王科技有限公司 | Preparation method of pigment yellow 180 mixed crystal |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1298416A (en) * | 1998-04-23 | 2001-06-06 | 纳幕尔杜邦公司 | Polyesters including isosorbide as a comonomer and methods for making same |
| CN1298343A (en) * | 1998-04-23 | 2001-06-06 | 纳幕尔杜邦公司 | Isosorbide containing polyesters and methods for making same |
| WO2003027119A1 (en) * | 2001-09-24 | 2003-04-03 | Koninklijke Philips Electronics N.V. | Isosorbide derivatives |
-
2005
- 2005-07-01 CN CNB2005100798949A patent/CN1298765C/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1298416A (en) * | 1998-04-23 | 2001-06-06 | 纳幕尔杜邦公司 | Polyesters including isosorbide as a comonomer and methods for making same |
| CN1298343A (en) * | 1998-04-23 | 2001-06-06 | 纳幕尔杜邦公司 | Isosorbide containing polyesters and methods for making same |
| WO2003027119A1 (en) * | 2001-09-24 | 2003-04-03 | Koninklijke Philips Electronics N.V. | Isosorbide derivatives |
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| CN1702096A (en) | 2005-11-30 |
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