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US4959451A
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Novel diallyl terephthalate prepolymer and method for preparing it
Assignee: Resonac Holdings Corp
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Filing: 1989-10-17
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Granted: 1990-09-25
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Expires: 2009-10-17
Abstract
Abstract A diallyl terephthalate prepolymer is here disclosed which essentially has the following structure CH.sub.2 ═CHCH.sub.2 O(COArCOOBO).sub.n COArCOOCH.sub.2 CH═CH.sub.2 wherein B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, Ar is a 1,4-phenylene group, and n is a value of 1 to 100, and having an unsaturation in a range of 20 to 100, as represented by an iodine value determine by the Wijs method, and there is also disclosed a method for preparing the diallyl terephthalate prepolymer. The method of the present invention permits obtaining the allyl prepolymer having excellent physical properties from inexpensive raw materials with less labor. Since this prepolymer has a double bond suitably, it can be mixed with unsaturated polyester resin or diallyl phthalate resin, when used. Moreover, the prepolymer can be also used as a crosslinking agent for EPR, elaslene, synthetic rubber and the like.
Inventors
- 👤 Hiroshi Uchida
- 👤 Kuniomi Marumo
- 👤 Shigehiro Chaen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 05:42
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/12; C08G63/46; C08G63/50; C08G63/52; C08G63/54; C08G63/547; C08F; C08F291/00; C08F291/02; C08F299/00; C08F299/02; C08F299/04; C08F299/0478; C08F299/0485; C08L; C08L67/00; C08L67/06; C08L67/07
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
67 words
A diallyl terephthalate prepolymer essentially having the following structure CH.sub.2 ═CHCH.sub.2 O(COArCOOBO).sub.n COArCOOCH.sub.2 CH═CH.sub.2 wherein B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, Ar is a 1,4-phenylene group, and n is a value of 1 to 100, and having an unsaturation in a range of 20 to 100, as represented by an iodine value determined by the Wijs method.
Claim 2
Dependent Claim
67 words
A diallyl terephthalate prepolymer essentially having the following structure CH.sub.2 ═CHCH.sub.2 O(COArCOOBO).sub.n COArCOOCH.sub.2 CH═CH.sub.2 wherein B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, Ar is a 1,4-phenylene group, and n is a value of 1 to 100, and having an unsaturation in a range of 20 to 100, as represented by an iodine value determined by the Wijs method.
Claim 3
Dependent Claim
133 words
A diallyl terephthalate prepolymer having an allyl ester group at its terminal, having the following repeating units --(COArCOOBO)-- moiety A --(COArCOO).sub.x --Z--O--COArCOO-- moiety B wherein x is a value of 2 to 10, Z is an organic residue derived from a polyol having 3 to 10 hydroxyl groups, B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, and Ar is a 1,4,-phenylene group, and having an unsaturation in a range of 20 to 100, as represented by an iodine value determined by the Wijs method, the mol fraction of the moiety A in the prepolymer portion exclusive of the terminal allyl groups being in a range of 10 to 98%, and the mol fraction of the moiety B being in a range of the remaining mol%.
Claim 4
Dependent Claim
133 words
A diallyl terephthalate prepolymer having an allyl ester group at its terminal, having the following repeating units --(COArCOOBO)-- moiety A --(COArCOO).sub.x --Z--O--COArCOO-- moiety B wherein x is a value of 2 to 10, Z is an organic residue derived from a polyol having 3 to 10 hydroxyl groups, B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, and Ar is a 1,4,-phenylene group, and having an unsaturation in a range of 20 to 100, as represented by an iodine value determined by the Wijs method, the mol fraction of the moiety A in the prepolymer portion exclusive of the terminal allyl groups being in a range of 10 to 98%, and the mol fraction of the moiety B being in a range of the remaining mol%.
Claim 5
Dependent Claim
57 words
A diallyl terephthalate prepolymer according to claim 1 or 2 wherein the number average molecular weight (Mn) is from 500 to 15,000 as polystyrene and the weight average molecular weight (Mw) is from 1,000 to 70,000 as polystyrene, and the Mw/Mn ratio is from 1.20 to 20.0, said Mn and Mw being determined by gel permeation chromatography.
Claim 6
Dependent Claim
25 words
A diallyl terephthalate prepolymer according to claim 3 wherein each of Z and B is a saturated aliphatic hydrocarbon having 2 to 10 carbon atoms.
Claim 7
Independent Claim
241 words
A method for preparing a diallyl terephthalate prepolymer essentially having the following structure CH.sub.2 ═CHCH.sub.2 O(COArCOOBO).sub.n COArCOOCH.sub.2 CH═CH.sub.2 wherein B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, Ar is a 1,4-phenylene group, and n is a value of 1 to 100, and having an unsaturation in a range of 20 to 100, as represented by the iodine value determined by the Wijs method, or a diallyl terephthalate prepolymer having an allyl ester group at its terminal, having the following repeating units --(COArCOOBO)-- moiety A --(COArCOO).sub.x --Z--O--COArCOO-- moiety B wherein X is a value of 2 to 10, Z is an organic residue derived from a polyol having 3 to 10 hydroxy groups, B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, and Ar is a 1,4-phenylene group, and having an unsaturation in a range of 20 to 100, as represented by the iodine value determined by the Wijs method, the mol fraction of the moiety A in the prepolymer portion exclusive of the terminal allyl groups being in a range of 10 to 98%, and the mol fraction of the moiety B being in a range of the remaining mol%, said method comprising reacting dimethyl terephthalate or diethyl terephthalate, one or more of divalent or higher-valent saturated aliphatic polyols and allyl alcohol in the presence of an ester exchange catalyst, while distilling off methanol or ethanol.
Claim 8
Independent Claim
241 words
A method for preparing a diallyl terephthalate prepolymer essentially having the following structure CH.sub.2 ═CHCH.sub.2 O(COArCOOBO).sub.n COArCOOCH.sub.2 CH═CH.sub.2 wherein B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, Ar is a 1,4-phenylene group, and n is a value of 1 to 100, and having an unsaturation in a range of 20 to 100, as represented by the iodine value determined by the Wijs method, or a diallyl terephthalate prepolymer having an allyl ester group at its terminal, having the following repeating units --(COArCOOBO)-- moiety A --(COArCOO).sub.x --Z--O--COArCOO-- moiety B wherein X is a value of 2 to 10, Z is an organic residue derived from a polyol having 3 to 10 hydroxy groups, B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, and Ar is a 1,4-phenylene group, and having an unsaturation in a range of 20 to 100, as represented by the iodine value determined by the Wijs method, the mol fraction of the moiety A in the prepolymer portion exclusive of the terminal allyl groups being in a range of 10 to 98%, and the mol fraction of the moiety B being in a range of the remaining mol%, said method comprising reacting dimethyl terephthalate or diethyl terephthalate, one or more of divalent or higher-valent saturated aliphatic polyols and allyl alcohol in the presence of an ester exchange catalyst, while distilling off methanol or ethanol.
Claim 9
Independent Claim
235 words
A method for preparing a diallyl terephthalate prepolymer essentially having the following structure CH.sub.2 ═CHCH.sub.2 O(COArCOOBO).sub.n COARCOOCH.sub.2 CH═CH.sub.2 wherein B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, Ar is a 1,4-phenylene group, and n is a value of 1 to 100, and having an unsaturation in a range of 20 to 100, as represented by the iodine value determined by the Wijs method, or a diallyl terephthalate prepolymer having an allyl ester group at its terminal, having the following repeating units --(COArCOOBO)-- moiety A --(COArCOO).sub.x --Z--O--COArCOO-- moiety B wherein X is a value of 2 to 10, Z is an organic residue derived from a polyol having 3 to 10 hydroxy groups, B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, and Ar is a 1,4-phenylene group, and having an unsaturation in a range of 20 to 100, as represented by the iodine value determined by the Wijs method, the mol fraction of the moiety A in the prepolymer portion exclusive of the terminal allyl groups being in the range of 10 to 98%, and the mol fraction of the moiety B being in a range of the remaining mol%, said method comprising reacting diallyl terephthalate and one or more of divalent or higher-valent saturated aliphatic polyols in the presence of an ester exchange catalyst, while distilling off allyl alcohol.
Claim 10
Independent Claim
235 words
A method for preparing a diallyl terephthalate prepolymer essentially having the following structure CH.sub.2 ═CHCH.sub.2 O(COArCOOBO).sub.n COARCOOCH.sub.2 CH═CH.sub.2 wherein B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, Ar is a 1,4-phenylene group, and n is a value of 1 to 100, and having an unsaturation in a range of 20 to 100, as represented by the iodine value determined by the Wijs method, or a diallyl terephthalate prepolymer having an allyl ester group at its terminal, having the following repeating units --(COArCOOBO)-- moiety A --(COArCOO).sub.x --Z--O--COArCOO-- moiety B wherein X is a value of 2 to 10, Z is an organic residue derived from a polyol having 3 to 10 hydroxy groups, B is a divalent organic residue derived from a diol having 2 to 20 carbon atoms, and Ar is a 1,4-phenylene group, and having an unsaturation in a range of 20 to 100, as represented by the iodine value determined by the Wijs method, the mol fraction of the moiety A in the prepolymer portion exclusive of the terminal allyl groups being in the range of 10 to 98%, and the mol fraction of the moiety B being in a range of the remaining mol%, said method comprising reacting diallyl terephthalate and one or more of divalent or higher-valent saturated aliphatic polyols in the presence of an ester exchange catalyst, while distilling off allyl alcohol.
Claim 11
Dependent Claim
55 words
A method for preparing a diallyl terephthalate prepolymer according to claim 5 or 6 wherein after the reacting, the method comprises isolating the prepolymer by distilling off diallyl terephthalate from the resulting reaction mixture under reduced pressure of 10 mmHg or less, followed by grinding the prepolymer into a powder by means of a grinder.
Claim 12
Dependent Claim
49 words
A method for preparing a diallyl terephthalate prepolymer according to claim 5 or 6 wherein after the reaction, the method comprises isolating the prepolymer by pouring the resulting reaction mixture into a solvent which is a poor solvent for the diallyl terephthalate prepolymer, and then powdering the reaction mixture.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-09-24 | 1994-03-26 | 1994-09-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-09-24 | 1998-03-26 | 1998-09-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-09-24 | 2002-03-26 | 2002-09-25 | $7700.00 | Window Closed / Lapsed |