US4322502A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Simultaneous expansion and cure of polyester resin composition
Assignee: Uniroyal Chemical Co Inc
•
Filing: 1980-09-11
•
Granted: 1982-03-30
•
Expires: 2000-09-11
Abstract
Abstract Unsaturated polyester resin in solution in ethylenically unsaturated copolymerizable monomer is moved with peroxide catalyst, organometallic promoter and certain hydrazine-type or hydrazone compounds. The liquid mixture expands and cures to provide a solid foamed resin.
Inventors
- 👤 Paul E. Stott
- 👤 Edward L. Wheeler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 01:39
CPC Classifications
C; C08; C08J; C08J9/00; C08J9/04; C08J9/06; C08J9/10; C08J2367/00; C08J2367/06
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
248 words
An expandable and curable polyester composition comprising a mixture of: (a) a liquid ethylenically unsaturated polyester resin composition having an acid number from greater than 0 to 150; (b) a peroxide; (c) an organometallic promoter for the peroxide; and (d) a hydrazine or hydrazone compound having the formula: RNHNH.sub.2 or RNHN═CR.sup.1 R.sup.2 wherein R is C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 6 cycloalkyl, C 7 -C 9 aralkyl or substituted C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 6 cycloalkyl or C 7 -C 9 aralkyl, the substituent being halogen, cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkoxycarbonyl; R 1 and R 2 are the same or different and are C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl, C 7 -C 9 alkaryl or substituted C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl or C 7 -C 9 alkaryl, the substituent being halogen, cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkoxycarbonyl, or one of R 1 or R 2 may be hydrogen, and R 1 and R 2 together with the common carbon atom may form C 3 to C 8 cycloalkyl or a bridged ring hydrocarbyl group having 7 to 10 carbon atoms.
Claim 2
Dependent Claim
248 words
An expandable and curable polyester composition comprising a mixture of: (a) a liquid ethylenically unsaturated polyester resin composition having an acid number from greater than 0 to 150; (b) a peroxide; (c) an organometallic promoter for the peroxide; and (d) a hydrazine or hydrazone compound having the formula: RNHNH.sub.2 or RNHN═CR.sup.1 R.sup.2 wherein R is C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 6 cycloalkyl, C 7 -C 9 aralkyl or substituted C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 6 cycloalkyl or C 7 -C 9 aralkyl, the substituent being halogen, cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkoxycarbonyl; R 1 and R 2 are the same or different and are C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl, C 7 -C 9 alkaryl or substituted C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl or C 7 -C 9 alkaryl, the substituent being halogen, cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkoxycarbonyl, or one of R 1 or R 2 may be hydrogen, and R 1 and R 2 together with the common carbon atom may form C 3 to C 8 cycloalkyl or a bridged ring hydrocarbyl group having 7 to 10 carbon atoms.
Claim 3
Dependent Claim
16 words
The composition of claim 1 wherein (d) is a hydrazine having the formula RNHNH 2 .
Claim 4
Dependent Claim
18 words
The composition of claim 1 wherein (d) is a hydrazone having the formula RNHN═CR 1 R 2 .
Claim 5
Dependent Claim
21 words
The composition of claim 2 wherein R is C 1 or C 12 alkyl, or C 5 to C 6 cycloalkyl.
Claim 6
Dependent Claim
59 words
The composition of claim 3 wherein R is C 2 to C 6 alkyl; at least one of R 1 and R 2 is C 1 to C 6 alkyl, C 5 to C 6 cycloalkyl or phenyl, or the ═CR 1 R 2 group forms a partially hydrogenated bridged ring aryl moiety having 9 to 10 carbon atoms.
Claim 7
Dependent Claim
43 words
The composition of claim 1 wherein the concentration of the organometallic promoter (c) is from 0.40 to 17.0 mmoles of metal, and that of the hydrazine or hydrazone (d) is from 0.1 to 30 mmoles, per 100 grams of polyester resin composition (a).
Claim 8
Dependent Claim
13 words
The composition of claim 1 wherein a surfactant is included in said mixture.
Claim 9
Dependent Claim
15 words
The composition of claim 2 wherein aldehyde or a ketone is included in said mixture.
Claim 10
Dependent Claim
22 words
The composition of claim 1 wherein the molar ratio of peroxide (b) to hydrazine or hydrazone (d) is from 0.08 to 7.0.
Claim 11
Dependent Claim
18 words
The composition of claim 1 wherein the acid number of (a) is from greater than 0 to 75.
Claim 12
Dependent Claim
12 words
The composition of claim 1 wherein the peroxide (b) is hydrogen peroxide.
Claim 13
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 1 and exposing the mixture to expanding and curing conditions.
Claim 14
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 2 and exposing the mixture to expanding and curing conditions.
Claim 15
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 3 and exposing the mixture to expanding and curing conditions.
Claim 16
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 4 and exposing the mixture to expanding and curing conditions.
Claim 17
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 5 and exposing the mixture to expanding and curing conditions.
Claim 18
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 6 and exposing the mixture to expanding and curing conditions.
Claim 19
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 7 and exposing the mixture to expanding and curing conditions.
Claim 20
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 8 and exposing the mixture to expanding and curing conditions.
Claim 21
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 9 and exposing the mixture to expanding and curing conditions.
Claim 22
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 10 and exposing the mixture to expanding and curing conditions.
Claim 23
Dependent Claim
28 words
A method of making an expanded and cured polyester resin composition comprising providing a mixture as in claim 11 and exposing the mixture to expanding and curing conditions.
Claim 24
Dependent Claim
33 words
The method as in claim 12 in which the resin (a), the organometallic promoter (c) and the hydrazine or hydrazone compound (d) are mixed first, and then the peroxide curative (b) is added.
Claim 25
Independent Claim
338 words
A method for making expanded and cured polyester resin composition comprising preparing a mixture of: (a) a liquid polyester resin composition comprising an unsaturated linear polyester resin of an alpha, beta-ethylenically unsaturated dicarboxylic acid and a glycol dissolved in an ethylenically unsaturated monomer, having an acid value of from greater than 0 to 75; (b) a peroxide; (c) an organometallic promoter for the peroxide; and (d) a hydrazine or hydrazone compound having the formula RNHNH.sub.2 or RNHN═CR.sup.1 R.sup.2 where R is C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 6 cycloalkyl, C 7 -C 9 aralkyl or substituted C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 6 cycloalkyl or C 7 -C 9 aralkyl, the substituent being halogen, cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkoxycarbonyl; R 1 and R 2 are the same or different and are C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl, C 7 -C 9 alkaryl or substituted C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl, C 7 -C 9 alkaryl, the substituent being halogen, cyano, C 1 -C 4 alkoxy or C 1 - C 4 alkoxycarbonyl, or one of R 1 or R 2 may be hydrogen, and R 1 and R 2 together with the common carbon atom may form C 3 to C 8 cycloalkyl or a bridged ring hydrocarbyl group having 7 to 10 carbon atoms, and exposing said mixture to expanding and curing conditions; the concentration of organometallic promoter (c) being from 0.40 to 17 mmoles of metal per 100 grams of resin (a); the concentration of hydrazine-type or hydrazone-type compound (d) being from 0.1 to 30 mmoles per 100 grams of resin (a); and the molar ratio of peroxide (b) to compound (d) being from 0.08 to 7.
Claim 26
Independent Claim
338 words
A method for making expanded and cured polyester resin composition comprising preparing a mixture of: (a) a liquid polyester resin composition comprising an unsaturated linear polyester resin of an alpha, beta-ethylenically unsaturated dicarboxylic acid and a glycol dissolved in an ethylenically unsaturated monomer, having an acid value of from greater than 0 to 75; (b) a peroxide; (c) an organometallic promoter for the peroxide; and (d) a hydrazine or hydrazone compound having the formula RNHNH.sub.2 or RNHN═CR.sup.1 R.sup.2 where R is C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 6 cycloalkyl, C 7 -C 9 aralkyl or substituted C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 6 cycloalkyl or C 7 -C 9 aralkyl, the substituent being halogen, cyano, C 1 -C 4 alkoxy or C 1 -C 4 alkoxycarbonyl; R 1 and R 2 are the same or different and are C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl, C 7 -C 9 alkaryl or substituted C 1 -C 16 alkyl, C 2 -C 16 alkenyl, C 5 -C 6 cycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl, C 7 -C 9 alkaryl, the substituent being halogen, cyano, C 1 -C 4 alkoxy or C 1 - C 4 alkoxycarbonyl, or one of R 1 or R 2 may be hydrogen, and R 1 and R 2 together with the common carbon atom may form C 3 to C 8 cycloalkyl or a bridged ring hydrocarbyl group having 7 to 10 carbon atoms, and exposing said mixture to expanding and curing conditions; the concentration of organometallic promoter (c) being from 0.40 to 17 mmoles of metal per 100 grams of resin (a); the concentration of hydrazine-type or hydrazone-type compound (d) being from 0.1 to 30 mmoles per 100 grams of resin (a); and the molar ratio of peroxide (b) to compound (d) being from 0.08 to 7.
Claim 27
Dependent Claim
58 words
A method as in claim 24 in which the resin (a) has an acid value of from 7.5 to 40, the concentration of the organometallic promoter (c) is from 0.70 to 7.0 mmoles of metal per 100 grams of resin (a) and the molar ratio of peroxide (b) to hydrazine or hydrazone (d) is from 1 to 3.
Claim 28
Dependent Claim
27 words
A method as in claim 25 in which the peroxide curative (b) is hydrogen peroxide and the promoter (c) is a cobalt salt of an organic acid.
Claim 29
Dependent Claim
44 words
A method as in claim 25 in which (d) is selected from t-butylhydrazine 5-methyl-2-hexanone-t-butylhydrazone monomethylhydrazine isobutylhydrazine sec.-pentylhydrazine decylhydrazine octadecylhydrazine benzylhydrazine cyanoethylhydrazine 2-propanone methyl hydrazone 2-butanone t-butyl hydrazone 3-pentanone t-butyl hydrazone 3,3-dimethyl-2-butanone t-butyl hydrazone acetophenone t-butyl hydrazone 2-undecanone t-butyl hydrazone methylhydrazine plus acetone and 4-methyl-2-pentylhydrazine.
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) | 1985-03-29 | 1985-09-28 | 1986-03-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-03-29 | 1989-09-28 | 1990-03-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-03-29 | 1993-09-28 | 1994-03-30 | $7700.00 | Window Closed / Lapsed |