US4683279A
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US
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Low melting urethane linked toluenediisocyanates
Assignee: Air Products and Chemicals Inc
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Filing: 1986-07-08
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Granted: 1987-07-28
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Expires: 2006-07-08
Abstract
Abstract This invention relates to urethane linked mixtures of 2,4- and 2,6-toluenediisocyanates (ULTDI dimers) having low melting points and to a method of forming these systems. The urethane linked toluenediisocyanates containing from 45-90% of the 2,4- and 10-55% of the 2,6- isomer by weight are formed by reacting two moles of an appropriate isomer mix of toluenediisocyanate, with one mole of a specific alkylene glycol, e.g., 1,2-butanediol, diethylene glycol or dipropylene glycol under conditions such that essentially only one of the isocyanate groups on a toluenediisocyanate molecule reacts with a hydroxyl group of the glycol. Conditions are controlled such that the urethane linked toluenediisocyanates are formed. The resulting product, which has two unreacted isocyanate groups, is suited for producing a variety of elastomers including polyurethane polyurethane/urea or polyurea elastomers.
Inventors
- 👤 Barton Milligan
- 👤 William E. Starner
- 👤 Roland E. Grandin
- 👤 Jeremiah P. Casey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 05:02
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/80; C08G18/8003; C08G18/8006; C08G18/8009; C08G18/8012; C08G18/8019; C08G18/81; C08G18/8141; C08G18/815; C08G2120/00
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
138 words
A process for producing a low melting urethane linked toluenediisocyanate which comprises the steps: (a) reacting an isomer mix of 2,4- and 2,6-toluene diisocyanate with a short chain diol selected from the group consisting of dipropylene glycol, diethylene glycol 1,2-butanediol, 1,4-but-2-ene diol, triethylene glycol and tripropylene glycol; (b) maintaining a temperature sufficient to effect reaction between a first isocyanate group of said toluenediisocyanate and a hydroxy group of said short chain diol, but insufficient for effecting reaction with a second isocyanate group on the toluenediisocyanate ring and a hydroxy group; (c) maintaining a stoichiometric excess of toluenediisocyanate to said diol (d) utilizing an isomer mix such that the reaction product contains from about 45 to 90% by weight of the 2,4-isomer and 10 to 55% of the 2,6-isomer; and (e) isolating the reaction product from the reaction medium.
Claim 2
Dependent Claim
138 words
A process for producing a low melting urethane linked toluenediisocyanate which comprises the steps: (a) reacting an isomer mix of 2,4- and 2,6-toluene diisocyanate with a short chain diol selected from the group consisting of dipropylene glycol, diethylene glycol 1,2-butanediol, 1,4-but-2-ene diol, triethylene glycol and tripropylene glycol; (b) maintaining a temperature sufficient to effect reaction between a first isocyanate group of said toluenediisocyanate and a hydroxy group of said short chain diol, but insufficient for effecting reaction with a second isocyanate group on the toluenediisocyanate ring and a hydroxy group; (c) maintaining a stoichiometric excess of toluenediisocyanate to said diol (d) utilizing an isomer mix such that the reaction product contains from about 45 to 90% by weight of the 2,4-isomer and 10 to 55% of the 2,6-isomer; and (e) isolating the reaction product from the reaction medium.
Claim 3
Dependent Claim
29 words
The process of claim 1 wherein the reaction temperature is maintained is from about -25° to about 90° C., and the oligomer content is less than 10% by weight.
Claim 4
Dependent Claim
22 words
The process of claim 2 wherein the mole ratio of said toluenediisocyanate to short chain diol using reactions is from about 4-30:1.
Claim 5
Dependent Claim
31 words
The process of claim 2 wherein the isomer mix is adjusted such that the reaction product has from 75 to 85% by weight of the 2,4-isomer and 15-25% of the 2,6-isomer.
Claim 6
Dependent Claim
31 words
The process of claim 4 wherein the mole ratio of toluenediisocyanate to diol is maintained at a level from 8-20:1 and the oligomer content is less than about 5% by weight.
Claim 7
Dependent Claim
10 words
The process of claim 4 wherein said diol is 1,2-butanediol.
Claim 8
Dependent Claim
11 words
The process of claim 4 wherein said diol is diethlylene glycol.
Claim 9
Dependent Claim
11 words
The process of claim 4 wherein said diol is dipropylene glycol.
Claim 10
Dependent Claim
11 words
The process of claim 4 wherein said diol is 1,4-but-2-ene diol.
Claim 11
Dependent Claim
163 words
A process for producing a low melting urethane linked toluenediisocyanate which comprises the steps: (a) reacting an isomer mix of 2,4- and 2,6-toluenediisocyanate with a short chain diol represented by the formula: OH--R--OH where R is a C 2-12 alkylene radical having one or more of the following characteristics: (a) one or more carbon-carbon unsaturated groups (b) alkyl side chains having 2-6 carbon atoms or (c) 1 to 3 ether oxygen atoms. (b) maintaining a temperature sufficient to effect reaction between a first isocyanate group of said toluenediisocyanate and a hydroxy group of said short chain diol, but insufficient for effecting reaction with a second isocyanate group on the toluenediisocyanate ring and a hydroxy group; (c) maintaining a stoichiometric excess of toluenediisocyanate to said diol (d) utilizing an isomer mix such that the reaction product contains from about 45 to 90% by weight of the 2,4-isomer and 10 to 55% of the 2,6-isomer; and (e) isolating the reaction product from the reaction medium.
Claim 12
Dependent Claim
163 words
A process for producing a low melting urethane linked toluenediisocyanate which comprises the steps: (a) reacting an isomer mix of 2,4- and 2,6-toluenediisocyanate with a short chain diol represented by the formula: OH--R--OH where R is a C 2-12 alkylene radical having one or more of the following characteristics: (a) one or more carbon-carbon unsaturated groups (b) alkyl side chains having 2-6 carbon atoms or (c) 1 to 3 ether oxygen atoms. (b) maintaining a temperature sufficient to effect reaction between a first isocyanate group of said toluenediisocyanate and a hydroxy group of said short chain diol, but insufficient for effecting reaction with a second isocyanate group on the toluenediisocyanate ring and a hydroxy group; (c) maintaining a stoichiometric excess of toluenediisocyanate to said diol (d) utilizing an isomer mix such that the reaction product contains from about 45 to 90% by weight of the 2,4-isomer and 10 to 55% of the 2,6-isomer; and (e) isolating the reaction product from the reaction medium.
Claim 13
Dependent Claim
29 words
The process of claim 10 wherein in step C the mole ratio of toluenediisocyanate to diol is from 8-20:1 and the oligomer content is less than 10% by weight.
Claim 14
Dependent Claim
29 words
The process of claim 11 wherein the isomer mix is adjusted such that the reaction product has from 75-85% by weight of the 2,4-isomer and 15-25% of the 2,6-isomer.
Claim 15
Dependent Claim
19 words
The process of claim 11 wherein R in said short chain diol is the residue from 1,2 butane diol.
Claim 16
Dependent Claim
18 words
The process of claim 11 wherein R in said short chain diol is the residue from diethylene glycol.
Claim 17
Dependent Claim
18 words
The process of claim 11 wherein R in said short chain diol is the residue from tripropylene glycol.
Claim 18
Dependent Claim
160 words
A low melting urethane linked toluenediisocyanate composition represented by the formula: ##STR2## where R is the residue of a nonsymmetric aliphatic diol or symmetric ether diol represented by the formula: OH--R--OH where R is C 2-12 alkylene radical having one or more of the following characteristics: (a) one or more carbon-carbon unsaturated groups (b) alkyl side chains having 2-6 carbon atoms or (c) 1 to 3 ether oxygen atoms, (b) maintaining a temperature sufficient to effect reaction between a first isocyanate group of said toluenediisocyanate and a hydroxy group of said short chain diol, but insufficient for effecting reaction with a second isocyanate group on the toluenediisocyanate ring and a hydroxy group; (c) maintaining a stoichiometric excess of toluenediisocyanate to said diol (d) utilizing an isomer mix such that the reaction product contains from about 45 to 90% by weight of the 2,4-isomer and 10 to 55% of the 2,6-isomer; and (e) isolating the reaction product from the reaction medium.
Claim 19
Dependent Claim
160 words
A low melting urethane linked toluenediisocyanate composition represented by the formula: ##STR2## where R is the residue of a nonsymmetric aliphatic diol or symmetric ether diol represented by the formula: OH--R--OH where R is C 2-12 alkylene radical having one or more of the following characteristics: (a) one or more carbon-carbon unsaturated groups (b) alkyl side chains having 2-6 carbon atoms or (c) 1 to 3 ether oxygen atoms, (b) maintaining a temperature sufficient to effect reaction between a first isocyanate group of said toluenediisocyanate and a hydroxy group of said short chain diol, but insufficient for effecting reaction with a second isocyanate group on the toluenediisocyanate ring and a hydroxy group; (c) maintaining a stoichiometric excess of toluenediisocyanate to said diol (d) utilizing an isomer mix such that the reaction product contains from about 45 to 90% by weight of the 2,4-isomer and 10 to 55% of the 2,6-isomer; and (e) isolating the reaction product from the reaction medium.
Claim 20
Dependent Claim
32 words
The low melting composition of claim 16 wherein R is the residue from a diol selected from the group consisting of 1,2-butanediol, diethylene glycol, 2-butene-1,4-diol, dipropylene glycol, triethylene glycol and tripropylene glycol.
Claim 21
Dependent Claim
41 words
The low melting composition of claim 16 wherein the weight percent of 2,4-isomer is from 45 to 90% and the weight percent of 2,6-isomer is from 10 to 55% and the reaction product has 10% or less by weight of oligomers.
Claim 22
Dependent Claim
29 words
The low melting composition of claim 18 wherein the percent 2,4-isomer by weight is from 65 to 80% and the percent 2,6-isomer by weight is from 20 to 35%.
Claim 23
Dependent Claim
14 words
The low melting composition of claim 16 where R is the residue from 1,2-butanediol.
Claim 24
Dependent Claim
15 words
The low melting composition of claim 16 wherein R is the residue from dipropylene glycol.
Claim 25
Dependent Claim
14 words
The low melting composition of claim 16 wherein R is the residue from diethyleneglycol.
Claim 26
Dependent Claim
15 words
The low melting composition of claim 16 wherein R is the residue from triethylene glycol.
Claim 27
Dependent Claim
15 words
The low melting composition of claim 16 wherein R is the residue from tripropylene glycol.
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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) | 1990-07-27 | 1991-01-26 | 1991-07-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-07-27 | 1995-01-26 | 1995-07-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-07-27 | 1999-01-26 | 1999-07-28 | $7700.00 | Window Closed / Lapsed |