CA2014291A1 - Substrat solide enrobe de cyclodextrine - Google Patents

Substrat solide enrobe de cyclodextrine

Info

Publication number: CA2014291A1
Authority: CA; Canada
Prior art keywords: diisocyanate; cyclodextrin; polyisocyanate; substrate; resin
Prior art date: 1990-04-10
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

Application number

CA002014291A

Other languages

English (en)

Inventor

Ronald P. Rohrbach

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

VOP

Honeywell UOP LLC

Original Assignee

VOP

UOP LLC

Priority date (The priority date 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 date listed.)

1990-04-10

Filing date

1990-04-10

Publication date

1991-10-10

1990-04-10 Application filed by VOP, UOP LLC filed Critical VOP

1990-04-10 Priority to CA002014291A priority Critical patent/CA2014291A1/fr

1990-04-10 Priority claimed from EP90303873A external-priority patent/EP0454910A1/fr

1991-10-10 Publication of CA2014291A1 publication Critical patent/CA2014291A1/fr

Status Abandoned legal-status Critical Current

Links

229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 112
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 63
239000000758 substrate Substances 0.000 title claims abstract description 39
239000007787 solid Substances 0.000 title claims abstract description 21
229920005989 resin Polymers 0.000 claims abstract description 39
239000011347 resin Substances 0.000 claims abstract description 39
239000005056 polyisocyanate Substances 0.000 claims abstract description 38
229920001228 polyisocyanate Polymers 0.000 claims abstract description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 15
239000002904 solvent Substances 0.000 claims abstract description 14
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 27
229960004853 betadex Drugs 0.000 claims description 27
239000001116 FEMA 4028 Substances 0.000 claims description 26
235000011175 beta-cyclodextrine Nutrition 0.000 claims description 26
238000000576 coating method Methods 0.000 claims description 17
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
239000011248 coating agent Substances 0.000 claims description 15
125000005442 diisocyanate group Chemical group 0.000 claims description 15
239000000047 product Substances 0.000 claims description 15
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
239000000010 aprotic solvent Substances 0.000 claims description 10
-1 boria Chemical compound 0.000 claims description 7
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 7
229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 6
229940043377 alpha-cyclodextrin Drugs 0.000 claims description 6
239000000919 ceramic Substances 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 5
239000004744 fabric Substances 0.000 claims description 5
239000000377 silicon dioxide Substances 0.000 claims description 5
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 4
229940080345 gamma-cyclodextrin Drugs 0.000 claims description 4
239000011521 glass Substances 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
150000002739 metals Chemical class 0.000 claims description 4
OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 3
CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 3
ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 claims description 3
DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 claims description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-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
239000004033 plastic Substances 0.000 claims description 3
229920003023 plastic Polymers 0.000 claims description 3
229920006389 polyphenyl polymer Polymers 0.000 claims description 3
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 claims description 3
VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims 4
SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 claims 2
HZVFICMRIHBAEK-UHFFFAOYSA-N 1-isocyanato-3-[(3-isocyanato-2-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=CC=C(N=C=O)C(C)=C1CC1=CC=CC(N=C=O)=C1C HZVFICMRIHBAEK-UHFFFAOYSA-N 0.000 claims 2
239000000395 magnesium oxide Substances 0.000 claims 2
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims 1
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims 1
238000000926 separation method Methods 0.000 abstract description 8
239000010409 thin film Substances 0.000 abstract description 5
230000001070 adhesive effect Effects 0.000 abstract description 3
238000011068 loading method Methods 0.000 abstract description 3
238000000746 purification Methods 0.000 abstract description 2
229940097362 cyclodextrins Drugs 0.000 description 24
239000000463 material Substances 0.000 description 21
239000000243 solution Substances 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 13
239000010408 film Substances 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
239000000123 paper Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000005755 formation reaction Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007790 solid phase Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000000151 deposition Methods 0.000 description 3
235000013305 food Nutrition 0.000 description 3
230000002209 hydrophobic effect Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000002023 wood Substances 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000000536 complexating effect Effects 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
239000011888 foil Substances 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052809 inorganic oxide Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000011368 organic material Substances 0.000 description 2
239000003973 paint Substances 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical class O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 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
241000207199 Citrus Species 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
241001440267 Cyclodes Species 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
101100166829 Mus musculus Cenpk gene Proteins 0.000 description 1
101100284914 Mus musculus Higd1c gene Proteins 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
244000309464 bull Species 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229910052729 chemical element Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
230000005660 hydrophilic surface Effects 0.000 description 1
230000005661 hydrophobic surface Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
239000011356 non-aqueous organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
229920005749 polyurethane resin Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000011819 refractory material Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Polysaccharides And Polysaccharide Derivatives (AREA)

CA002014291A 1990-04-10 1990-04-10 Substrat solide enrobe de cyclodextrine Abandoned CA2014291A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002014291A CA2014291A1 (fr)	1990-04-10	1990-04-10	Substrat solide enrobe de cyclodextrine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP90303873A EP0454910A1 (fr)	1988-07-11	1990-04-10	Substrat solide revêtu de cyclodextrine
CA002014291A CA2014291A1 (fr)	1990-04-10	1990-04-10	Substrat solide enrobe de cyclodextrine

Publications (1)

Publication Number	Publication Date
CA2014291A1 true CA2014291A1 (fr)	1991-10-10

Family

ID=25674062

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002014291A Abandoned CA2014291A1 (fr)	1990-04-10	1990-04-10	Substrat solide enrobe de cyclodextrine

Country Status (1)

Country	Link
CA (1)	CA2014291A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116574440A (zh) *	2023-04-26	2023-08-11	广州市百庄复合材料有限公司	一种水性保护剂及其制备方法

1990
- 1990-04-10 CA CA002014291A patent/CA2014291A1/fr not_active Abandoned

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN116574440A (zh) *	2023-04-26	2023-08-11	广州市百庄复合材料有限公司	一种水性保护剂及其制备方法
CN116574440B (zh) *	2023-04-26	2024-01-19	广州市百庄复合材料有限公司	一种水性保护剂及其制备方法

Legal Events

Date	Code	Title	Description
1992-10-12	FZDE	Discontinued

Publication	Publication Date	Title
US4917956A (en)	1990-04-17	Method of preparing cyclodextrin-coated surfaces
US5098793A (en)	1992-03-24	Cyclodextrin films on solid substrates
DE3007869C2 (fr)	1990-02-01
Arnold et al.	1971	Unusual film‐forming properties of aromatic heterocyclic ladder polymers
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WO1998022197A9 (fr)	1998-09-11	Matieres de separation en polymeres de cyclodextrine
WO1998022197A1 (fr)	1998-05-28	Matieres de separation en polymeres de cyclodextrine
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US8007911B2 (en)	2011-08-30	Material for room temperature curable solvent-borne overcoating material,coating material using same and coating film
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