US4816543A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyurethane system using monotertiary-alkyltoluenediamine as a cross linker
Assignee: Air Products and Chemicals Inc
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Filing: 1985-08-23
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Granted: 1989-03-28
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Expires: 2005-08-23
Abstract
Abstract This invention relates to improved polyurethane systems prepared by reacting an organic polyisocyanate with a hydroxyl containing compound, the improvement comprising utilizing mono tertiary-alkyltoluenediamine where the tertiary-alkyl group is ortho to an amine group as a chain extender or component thereof. The ortho-tertiary-butyltoluenediamine isomer is particular effective for use in reaction injection molding of polyurethanes and can be formulated with polyol as a chain extender mix.
Inventors
- 👤 William F. Burgoyne, Jr.
- 👤 Jeremiah P. Casey
- 👤 Dale D. Dixon
- 👤 Barton Milligan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 16:09
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/20; C08G18/28; C08G18/65; C08G18/66; C08G18/6603; C08G18/6614; C08G18/6618; C08G18/10; C08G18/30; C08G18/32; C08G18/3225; C08G18/3237; C08G18/324; C08G2120/00
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
119 words
In a process for the production of polyurethane-urea elastomers comprising the steps of reacting: (a) an organic polyisocyanate with: (b) an organic compound having a molecular weight from about 400 to 12,000 and containing at least two Zerewitinoff active hydrogen atoms; and (c) an aromatic diamine chain extending agent; and curing the resultant reaction product, the improvement wherein at least a portion of the aromatic diamine used as said chain extender is a mono-tertiary-alkyltoluenediamine where the tertiary-alkyl group is ortho to an amine group and represented by the formula: ##STR2## wherein R 1 , R 2 and R 3 are C 1-3 alkyl groups or R 2 and R 3 are combined to form a C 5-6 membered ring.
Claim 2
Dependent Claim
119 words
In a process for the production of polyurethane-urea elastomers comprising the steps of reacting: (a) an organic polyisocyanate with: (b) an organic compound having a molecular weight from about 400 to 12,000 and containing at least two Zerewitinoff active hydrogen atoms; and (c) an aromatic diamine chain extending agent; and curing the resultant reaction product, the improvement wherein at least a portion of the aromatic diamine used as said chain extender is a mono-tertiary-alkyltoluenediamine where the tertiary-alkyl group is ortho to an amine group and represented by the formula: ##STR2## wherein R 1 , R 2 and R 3 are C 1-3 alkyl groups or R 2 and R 3 are combined to form a C 5-6 membered ring.
Claim 3
Dependent Claim
33 words
The process of claim 1 wherein at least 50% of the equivalent weight of the total amount of aromatic diamine chain extender employed for reaction with the free-isocyanate is provided by the tertiary-alkyltoluenediamine.
Claim 4
Dependent Claim
50 words
The process of claim 2 wherein the polyurethane-urea elastomer is formed by reacting the isocyanate with said orgaic compound to form a prepolymer, said prepolymer having a free isocyanate content from about 5 to 25% by weight and then reacting said prepolymer with said aromatic diamine chain extender comprising mono-tertiary-alkyltoluenediamine.
Claim 5
Dependent Claim
10 words
The process of claim 3 wherein the mono-tertiary-alkyltoluenediamine is 2,6-diamino-3-tert-butyltoluene.
Claim 6
Dependent Claim
10 words
The process of claim 3 wherein said mono-tertiary-alkyltoluene-diamine is 2,6-diamino-3-tert-alkyltoluene.
Claim 7
Dependent Claim
11 words
The process of claim 4 wherein said isocyanate is 4,4'-methylene bis(phenylisocyanate).
Claim 8
Dependent Claim
30 words
The process of claim 3 wherein the mono-tertiary butyltoluenediamine is a mixture containing from about 65 to 80% by weight of 2,4-diamino-5-tert-butyltoluene and 20 to 35% by weight of 2,6-diamino-3-tert-butyltoluene.
Claim 9
Dependent Claim
14 words
The process of claim 2 wherein said organic compound is an aminated polyether polyol.
Claim 10
Dependent Claim
24 words
The process of claim 8 wherein said mono-tertiary-alkyltoluenediamine is selected from the group consisting of 2,6-diamino-3 tert-butyltoluene, 2,4-diamino-5-tert-butyltoluene. 3-tert-amyl-2,6-toluenediamine, 5-tert-amyl-2,4-toluenediamine, 3-tert-methylcyclohexyl-2,4-toluenediamine and 5-tert-methyl cyclohexyl-2,4-toluenediamine.
Claim 11
Dependent Claim
12 words
The process of claim 9 wherein said organic polyisocyanate is 4,4'-methylene-bis (phenylisocyanate).
Claim 12
Dependent Claim
37 words
In a polyurea composition formed by reacting an organic polyisocyanate with an amine terminated polyol or amine terminated polyester polyol and an aromatic diamine chain extender, the improvement which comprises as said chain extender 5-tert-butyl-2,4-toluenediamine or 3-tert-butyl-2,6-toluenediamine.
Claim 13
Dependent Claim
37 words
In a polyurea composition formed by reacting an organic polyisocyanate with an amine terminated polyol or amine terminated polyester polyol and an aromatic diamine chain extender, the improvement which comprises as said chain extender 5-tert-butyl-2,4-toluenediamine or 3-tert-butyl-2,6-toluenediamine.
Claim 14
Dependent Claim
88 words
In a process of production of polyurethane elastomer moldings by a reaction injection molding process wherein an aromatic polyisocyanate, a hydroxy containing compound having molecular weights from about 400 to 12,000, an aromatic diamine chain extender, and catalyst for enhancing the reaction between the hydroxyl group and the isocyanate are mixed, injected into a mold, reacted and cured, the improvement which comprises including 2,6-diamino-3-C 4 -C 7 -tertalkyltoluene and is used in amount of at least 50% the equivalent weight of the aromatic diamine chain extending agent used.
Claim 15
Dependent Claim
88 words
In a process of production of polyurethane elastomer moldings by a reaction injection molding process wherein an aromatic polyisocyanate, a hydroxy containing compound having molecular weights from about 400 to 12,000, an aromatic diamine chain extender, and catalyst for enhancing the reaction between the hydroxyl group and the isocyanate are mixed, injected into a mold, reacted and cured, the improvement which comprises including 2,6-diamino-3-C 4 -C 7 -tertalkyltoluene and is used in amount of at least 50% the equivalent weight of the aromatic diamine chain extending agent used.
Claim 16
Dependent Claim
11 words
The process of claim 12 wherein the chain extender is 3-tert-butyl-2,6-diaminotoluene.
Claim 17
Dependent Claim
34 words
The process of claim 12 wherein the chain extender system comprises a mix of aromatic diamine and polyol hydroxy containing compound, said hydroxyl containing compound having a molecular weight from about 400 to 12,000.
Claim 18
Dependent Claim
20 words
The process of claim 14 wherein the hydroxyl containing compound is a polyether, polythioether, polyacetal, polycarbonate, or a polyester polyol.
Claim 19
Dependent Claim
12 words
The process of claim 12 wherein the isocyanate employed is 4,4'-methylene bis(phenylisocyanate).
Claim 20
Dependent Claim
42 words
In a polyurethane composition formed by reacting an organic polyisocyanate with a hydroxyl containing compound having a molecular weight of from 400 to about 12,000 and an aromatic diamine chain extender the improvement wherein said aromatic diamine chain extending agent includes 2,6-diamino-3-tert-butyltoluene.
Claim 21
Dependent Claim
42 words
In a polyurethane composition formed by reacting an organic polyisocyanate with a hydroxyl containing compound having a molecular weight of from 400 to about 12,000 and an aromatic diamine chain extender the improvement wherein said aromatic diamine chain extending agent includes 2,6-diamino-3-tert-butyltoluene.
Claim 22
Dependent Claim
23 words
The composition of claim 17 wherein the monotert-butyl toluenediamine is 3-tert-butyl-2,6-diaminotoluene or a mixture containing from 65 to 80% by weight of 5-tert-butyl-2,4-diaminotoluene.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-03-27 | 1992-09-26 | 1993-03-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-03-27 | 1996-09-26 | 1997-03-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-03-27 | 2000-09-26 | 2001-03-28 | $7700.00 | Window Closed / Lapsed |