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US4490518A
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Liquid organic polyisocyanate-dicarboxylic ester binder composition and lignocellulosic composite materials prepared therefrom
Assignee: Olin Corp
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Filing: 1983-10-03
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Granted: 1984-12-25
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Expires: 2003-10-03
Abstract
Abstract Disclosed is a liquid binder composition containing from about 40 to about 98 percent by weight of an organic polyisocyanate and correspondingly from about 2 to about 60 percent by weight of a select ester derived from a dicarboxylic acid. When the binder composition is used in making lignocellulosic composite materials, such as particle board, the ester acts as an effective internal mold release agent, facilitating release of the composite material from the mold.
Inventors
- 👤 Stephen Fuzesi
- 👤 Robert W. Brown
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 13:39
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/28; C08G18/40; C08G18/64; C08G18/6484; C08L; C08L97/00; C08L97/02; C08G2125/00
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
222 words
A liquid binder composition comprising a mixture of from about 40 to about 98 percent by weight of an organic polyisocyanate and correspondingly from about 2 to about 60 percent by weight of an ester derived from a dicarboxylic acid, said ester being selected from the group consisting of (a) saturated aliphatic dicarboxylic esters having the formula ##STR4## wherein R 1 and R 2 are independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 haloalkyl and C 1 -C 20 alkoxy and n is an integer ranging from 1-12, inclusive; (b) unsaturated aliphatic dicarboxylic esters having the formula ##STR5## wherein R 3 and R 4 are independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 haloalkyl and C 1 -C 20 alkoxy and m and p are the same and each is an integer ranging from 1-10, inclusive; (c) aromatic dicarboxylic esters having the formula ##STR6## wherein R 5 and R 6 are independently selected from the group consisting of C 1 -C 10 alkyl, C 1 -C 10 haloalkyl and C 1 -C 10 alkoxy and wherein the aromatic ring is otherwise unsubstituted or substituted with at least one member selected from the group consisting of halo and C 1 -C 4 alkyl; and (d) mixtures threof.
Claim 2
Dependent Claim
222 words
A liquid binder composition comprising a mixture of from about 40 to about 98 percent by weight of an organic polyisocyanate and correspondingly from about 2 to about 60 percent by weight of an ester derived from a dicarboxylic acid, said ester being selected from the group consisting of (a) saturated aliphatic dicarboxylic esters having the formula ##STR4## wherein R 1 and R 2 are independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 haloalkyl and C 1 -C 20 alkoxy and n is an integer ranging from 1-12, inclusive; (b) unsaturated aliphatic dicarboxylic esters having the formula ##STR5## wherein R 3 and R 4 are independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 haloalkyl and C 1 -C 20 alkoxy and m and p are the same and each is an integer ranging from 1-10, inclusive; (c) aromatic dicarboxylic esters having the formula ##STR6## wherein R 5 and R 6 are independently selected from the group consisting of C 1 -C 10 alkyl, C 1 -C 10 haloalkyl and C 1 -C 10 alkoxy and wherein the aromatic ring is otherwise unsubstituted or substituted with at least one member selected from the group consisting of halo and C 1 -C 4 alkyl; and (d) mixtures threof.
Claim 3
Dependent Claim
156 words
The composition of claim 1, wherein said ester is selected from the group consisting of (a) saturated aliphatic dicarboxylic esters, wherein R 1 and R 2 are independently selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 haloalkyl and C 1 -C 8 alkoxy and n is an integer ranging from 1-8, inclusive; (b) unsaturated aliphatic dicarboxylic esters, wherein R 3 and R 4 are independently selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 haloalkyl and C 1 -C 8 alkoxy and m and p are the same and each is an integer ranging from 1-3, inclusive; (c) aromatic dicarboxylic esters, wherein R 5 and R 6 are independently selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy and wherein the aromatic ring is otherwise unsubstituted; and (d) mixtures thereof.
Claim 4
Dependent Claim
35 words
The composition of claim 2, wherein said ester is derived from a dicarboxylic acid selected from the group consisting of oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, maleic, fumaric, phthalic, isophthalic and terephthalic.
Claim 5
Dependent Claim
24 words
The composition of claim 3, wherein said ester is derived from a dicarboxylic acid selected from the group consisting of succinic, glutaric and adipic.
Claim 6
Dependent Claim
24 words
The composition of claim 1, wherein said organic polyisocyanate is selected from the group consisting of toluene diisocyanate, polyphenylene polymethylene isocyanate and mixtures thereof.
Claim 7
Dependent Claim
19 words
The composition of claim 5, wherein said organic polyisocyanate is a crude product of the phosgenation of toluene diamine.
Claim 8
Dependent Claim
39 words
The composition of claim 1, wherein there is employed in said mixture from about 70 to about 97 percent by weight of said organic polyisocyanate and correspondingly from about 3 to about 30 percent by weight of said ester.
Claim 9
Dependent Claim
49 words
The composition of claim 7, wherein said organic polyisocyanate is a crude product of the phosgenation of toluene diamine and said ester is derived from a dicarboxylic acid selected from the group consisting of oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, maleic, fumaric, phthalic, isophthalic and terephthalic.
Claim 10
Dependent Claim
116 words
The composition of claim 8, wherein said crude product is prepared by: (a) mixing toluene diamine with an inert organic diluent and a stoichiometric excess of phosgene; (b) heating the mixture to about 100°-200° C. in order to bring about the phosgenation of said toluene diamine to toluene diisocyanate, with the concurrent formation of hydrogen chloride as a by-product; (c) removing substantially all of the diluent, the unreacted phosgene and the hydrogen chloride by-product; (d) optionally removing, by distillation, a portion of the toluene diisocyanate in the phosgenation product and recovering, as a residual distilland, said crude phosgenation product; and (e) removing any precipitated or suspended solids that may be present in said crude phosgenation product.
Claim 11
Dependent Claim
24 words
The composition of claim 9, wherein said ester is derived from a dicarboxylic acid selected from the group consisting of succinic, glutaric and adipic.
Claim 12
Dependent Claim
264 words
A process for the preparation of a lignocellulosic composite material, comprising the steps of: contacting a plurality of lignocellulosic particles with a liquid binder composition; and then forming said contacted particles into a composite material by the application of heat and pressure, said liquid binder composition comprising a mixture of from about 40 to about 98 percent by weight of an organic polyisocyanate and correspondingly from about 2 to about 60 percent by weight of an ester derived from a dicarboxylic acid, said ester being selected from the group consisting of (a) saturated aliphatic dicarboxilic esters having the formula ##STR7## wherein R 1 and R 2 are independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 haloalkyl and C 1 -C 20 alkoxy and n is an integer ranging from 1-12, inclusive; (b) unsaturated aliphatic dicarboxylic esters having the formula ##STR8## wherein R 3 and R 4 are independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 haloalkyl and C 1 -C 20 alkoxy and m and p are the same and each is an integer ranging from 1-10, inclusive; (c) aromatic dicarboxic esters having the formula ##STR9## wherein R 5 and R 6 are independently selected from the group consisting of C 1 -C 10 alkyl, C 1 -C 10 haloalkyl and C 1 -C 10 alkoxy and wherein the aromatic ring is otherwise unsubstituted or substituted with at least one member selected from the group consisting of halo and C 1 -C 4 alkyl; and (d) mixtures thereof.
Claim 13
Dependent Claim
264 words
A process for the preparation of a lignocellulosic composite material, comprising the steps of: contacting a plurality of lignocellulosic particles with a liquid binder composition; and then forming said contacted particles into a composite material by the application of heat and pressure, said liquid binder composition comprising a mixture of from about 40 to about 98 percent by weight of an organic polyisocyanate and correspondingly from about 2 to about 60 percent by weight of an ester derived from a dicarboxylic acid, said ester being selected from the group consisting of (a) saturated aliphatic dicarboxilic esters having the formula ##STR7## wherein R 1 and R 2 are independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 haloalkyl and C 1 -C 20 alkoxy and n is an integer ranging from 1-12, inclusive; (b) unsaturated aliphatic dicarboxylic esters having the formula ##STR8## wherein R 3 and R 4 are independently selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 haloalkyl and C 1 -C 20 alkoxy and m and p are the same and each is an integer ranging from 1-10, inclusive; (c) aromatic dicarboxic esters having the formula ##STR9## wherein R 5 and R 6 are independently selected from the group consisting of C 1 -C 10 alkyl, C 1 -C 10 haloalkyl and C 1 -C 10 alkoxy and wherein the aromatic ring is otherwise unsubstituted or substituted with at least one member selected from the group consisting of halo and C 1 -C 4 alkyl; and (d) mixtures thereof.
Claim 14
Dependent Claim
31 words
The process of claim 11, wherein there is employed from about 2 to about 50 percent by weight, based on the dry weight of said lignocellulosic particles, of said binder composition.
Claim 15
Dependent Claim
31 words
The process of claim 12, wherein there is employed from about 3 to about 20 percent by weight, based on the dry weight of said lignocellulosic particles, of said binder composition.
Claim 16
Dependent Claim
156 words
The process of claim 11, wherein said ester is selected from the group consisting of (a) saturated aliphatic dicarboxylic esters, wherein R 1 and R 2 are independently selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 haloalkyl and C 1 -C 8 alkoxy and n is an integer ranging from 1-8, inclusive; (b) unsaturated aliphatic dicarboxylic esters, wherein R 3 and R 4 are independently selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 8 haloalkyl and C 1 -C 8 alkoxy and m and p are the same and each is an integer ranging from 1--3, inclusive; (c) aromatic dicarboxylic esters, wherein R 5 and R 6 are independently selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy and wherein the aromatic ring is otherwise unsubstituted; and (d) mixtures thereof.
Claim 17
Dependent Claim
35 words
The process of claim 14, wherein said ester is derived from a dicarboxylic acid selected from the group consisting of oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, maleic, fumaric, phthalic, isophthalic and terephthalic.
Claim 18
Dependent Claim
24 words
The process of claim 15, wherein said ester is derived from a dicarboxylic acid selected from the group consisting of succinic, glutaric and adipic.
Claim 19
Dependent Claim
24 words
The process of claim 11, wherein said organic polyisocyanate is selected from the group consisting of toluene diisocyanate, polyphenylene polymethylene isocyanate and mixtures thereof.
Claim 20
Dependent Claim
19 words
The process of claim 17, wherein said organic polyisocyanate is a crude product of the phosgenation of toluene diamine.
Claim 21
Dependent Claim
39 words
The process of claim 11, wherein there is employed in said mixture from about 70 to about 97 percent by weight of said organic polyisocyanate and correspondingly from about 3 to about 30 percent by weight of said ester.
Claim 22
Dependent Claim
49 words
The process of claim 19, wherein said organic polyisocyanate is a crude product of the phosgenation of toluene diamine and said ester is derived from a dicarboxylic acid selected from the group consisting of oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, maleic, fumaric, phthalic, isophthalic and terephthalic.
Claim 23
Dependent Claim
31 words
The process of claim 20, wherein there is employed from about 3 to about 20 percent by weight, based on the dry weight of said lignocellulosic particles, of said binder composition.
Claim 24
Dependent Claim
116 words
The process of claim 21, wherein said crude product is prepared by: (a) mixing toluene diamine with an inert organic diluent and a stoichiometric excess of phosgene; (b) heating the mixture to about 100°-200° C. in order to bring about the phosgenation of said toluene diamine to toluene diisocyanate, with the concurrent formation of hydrogen chloride as a by-product; (c) removing substantially all of the diluent, the unreacted phosgene and the hydrogen chloride by-product; (d) optionally removing, by distillation, a portion of the toluene diisocyanate in the phosgenation product and recovering, as a residual distilland, said crude phosgenation product; and (e) removing any precipitated or suspended solids that may be present in said crude phosgenation product.
Claim 25
Dependent Claim
24 words
The process of claim 22, wherein said ester is derived from a dicarboxylic acid selected from the group consisting of succinic, glutaric and adipic.
Claim 26
Dependent Claim
21 words
The process of claim 23, wherein said lignocellulosic particles are wood chips and said lignocellulosic composite material is wood particle board.
Claim 27
Dependent Claim
12 words
A lignocellulosic composite material prepared according to the process of claim 11.
Claim 28
Dependent Claim
12 words
A lignocellulosic composite material prepared according to the process of claim 16.
Claim 29
Dependent Claim
12 words
A lignocellulosic composite material prepared according to the process of claim 18.
Claim 30
Dependent Claim
12 words
A lignocellulosic composite material prepared according to the process of claim 20.
Claim 31
Dependent Claim
12 words
A lignocellulosic composite material prepared according to the process of claim 22.
Claim 32
Dependent Claim
12 words
A lignocellulosic composite material prepared according to the process of claim 23.
Claim 33
Dependent Claim
12 words
A lignocellulosic composite material prepared according to the process of claim 24.
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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) | 1987-12-25 | 1988-06-25 | 1988-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-25 | 1992-06-25 | 1992-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-25 | 1996-06-25 | 1996-12-25 | $7700.00 | Window Closed / Lapsed |