US4640801A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Graft polyols
Assignee: Rutherford Chemicals LLC
•
Filing: 1984-12-12
•
Granted: 1987-02-03
•
Expires: 2004-12-12
Abstract
Abstract Graft polyols comprising the liquid reaction product of a vegetable oil or unsaturated fatty carbon compound having at least eight carbon atoms, at least one hydroxyl group, and at least one double bond, a cyclopentadienyl compound and a terminally unsaturated monomer having at least one hydroxyl group. These liquid low viscosity polyols when cured with a polyisocyanate, melamine, or formaldehyde compound yield high solids or solventless polyurenthane compositions useful as coatings, adhesives, potting or molding compounds.
Inventors
- 👤 Dominic Simone
- 👤 Melvin Brauer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 19:24
CPC Classifications
C; C08; C08F; C08F242/00
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
63 words
A graft polyol comprising the liquid reaction product of: (a) at least one unsaturated fatty carbon compound having at least 8 carbon atoms, at least one hydroxyl group, and at least one ethylenic double bond, said compound having other than terminal unsaturation; (b) at least one liquid cyclopentadienyl compound; and (c) at least one terminally unsaturated monomer having at least one hydroxyl group.
Claim 2
Dependent Claim
63 words
A graft polyol comprising the liquid reaction product of: (a) at least one unsaturated fatty carbon compound having at least 8 carbon atoms, at least one hydroxyl group, and at least one ethylenic double bond, said compound having other than terminal unsaturation; (b) at least one liquid cyclopentadienyl compound; and (c) at least one terminally unsaturated monomer having at least one hydroxyl group.
Claim 3
Dependent Claim
16 words
The graft polyol according to claim 1 wherein the unsaturated fatty carbon compound is castor oil.
Claim 4
Dependent Claim
24 words
The graft polyol according to claim 1 wherein the terminally unsaturated hydroxyl monomer is a monoester of acrylic or methacrylic acid and a diol.
Claim 5
Dependent Claim
47 words
The graft polyol acording to claim 1 wherein the terminally unsaturated hydroxyl monomer is allyl alcohol, or an acrylic, methacrylic or crotonic acid monoester of ethylene glycol, propylene glycol, 1-4 butanediol, 1-6 hexanediol, 2,2 dimethyl-1,3-propanediol, 1-4 cyclohexane dimethanol, diethylene glycol, triethylene glycol, dipropylene glycol, or tripropylene glycol.
Claim 6
Dependent Claim
21 words
The graft polyol according to claim 1 wherein the terminally unsaturated hydroxyl monomer is allyl alcohol, hydroxyethyl acrylate or hydroxyethyl methacrylate.
Claim 7
Dependent Claim
30 words
The graft polyol according to claim 1 wherein the cyclopentadienyl compound is cyclopentadiene, methyl cyclopentadiene, dicyclopentadiene, methyl cyclopentadiene dimer, and mixtures of these compounds or their low molecular weight copolymers.
Claim 8
Dependent Claim
56 words
The graft polyol according to claim 1 wherein the unsaturated fatty carbon compound is present in an amount of about 50 to 90 percent, the cyclopentadienyl compound is present in an amount of 5 to 40 weight percent, and the terminally unsaturated hydroxyl monomer is present in an amount of about 1 to 25 weight percent.
Claim 9
Dependent Claim
35 words
A graft polyol comprised of about 50 to 90 weight percent castor oil, 5 to 40 weight percent cyclopentadiene or dicyclopentadiene, and 1 to 25 weight percent of hydroxyethyl methacrylate, hydroxyethyl acrylate or allyl alcohol.
Claim 10
Dependent Claim
35 words
A graft polyol comprised of about 50 to 90 weight percent castor oil, 5 to 40 weight percent cyclopentadiene or dicyclopentadiene, and 1 to 25 weight percent of hydroxyethyl methacrylate, hydroxyethyl acrylate or allyl alcohol.
Claim 11
Dependent Claim
88 words
A process for preparing a graft polyol liquid reaction product which comprises: (a) placing (i) at least one unsaturated fatty carbon compound having at least eight carbon atoms, at least one hydroxyl group, and at least one ethylenic double bond, said compound having other than terminal unsaturation (ii) one cyclopentradienyl compound, and (iii) at least one terminally unsaturated hydroxyl monomer in a pressurized reactor to form a mixture; and (b) heating this mixture at 250°-275° C. for a sufficient time to form a graft polyol liquid reaction product.
Claim 12
Dependent Claim
88 words
A process for preparing a graft polyol liquid reaction product which comprises: (a) placing (i) at least one unsaturated fatty carbon compound having at least eight carbon atoms, at least one hydroxyl group, and at least one ethylenic double bond, said compound having other than terminal unsaturation (ii) one cyclopentradienyl compound, and (iii) at least one terminally unsaturated hydroxyl monomer in a pressurized reactor to form a mixture; and (b) heating this mixture at 250°-275° C. for a sufficient time to form a graft polyol liquid reaction product.
Claim 13
Dependent Claim
18 words
The process according to claim 9 which further comprises removing air from the reactor before heating the mixture.
Claim 14
Dependent Claim
26 words
The process according to claim 10 which further comprises preheating the mixture from 50° to 150° C. to assist in removal of air from the reactor.
Claim 15
Dependent Claim
27 words
The process according to claim 11 which further comprises sparging with nitrogen with or without agitation during the preheating step to assist in the removal of air.
Claim 16
Dependent Claim
104 words
A process for preparing a graft polyol liquid reaction product which comprises: (a) placing in a pressurized reaction at least one unsaturated fatty carbon compound having at least eight carbon atoms, at least one hydroxyl group, and at least one ethylenic double bond, said compound having other than terminal unsaturation; (b) preheating the unsaturated fatty carbon compound; (c) adding at least one liquid cyclopentadienyl compound and at least one terminally unsaturated hydroxyl monomer to the preheated unsaturated fatty carbon compound to form a mixture; and (d) heating this mixture at 250°-275° C. for a sufficient time to form a graft polyol liquid reaction product.
Claim 17
Dependent Claim
104 words
A process for preparing a graft polyol liquid reaction product which comprises: (a) placing in a pressurized reaction at least one unsaturated fatty carbon compound having at least eight carbon atoms, at least one hydroxyl group, and at least one ethylenic double bond, said compound having other than terminal unsaturation; (b) preheating the unsaturated fatty carbon compound; (c) adding at least one liquid cyclopentadienyl compound and at least one terminally unsaturated hydroxyl monomer to the preheated unsaturated fatty carbon compound to form a mixture; and (d) heating this mixture at 250°-275° C. for a sufficient time to form a graft polyol liquid reaction product.
Claim 18
Dependent Claim
20 words
The process according to claim 13 wherein the unsaturated fatty carbon compound is preheated to between 50° and 150° C.
Claim 19
Dependent Claim
20 words
The process according to claim 13 wherein the unsaturated fatty carbon compound is preheated to between 250° and 275° C.
Claim 20
Dependent Claim
36 words
The process according to claim 13 wherein at least one liquid cyclopentadienyl compound and at least one terminally unsaturated hydroxyl monomer individually or jointly are added to the unsaturated fatty carbon compound by aliquots or continuously.
Claim 21
Dependent Claim
18 words
The process according to claim 13 which further comprises removing air from the reactor before heating the mixture.
Claim 22
Dependent Claim
27 words
The process according to claim 17 which further comprises sparging with nitrogen with or without agitation during the preheating step to assist in the removal of air.
Claim 23
Dependent Claim
57 words
A process for preparing a graft polyol which comprises: (a) placing castor oil in a pressurized reactor, (b) adding cyclopentadiene or dicyclopentadiene, and allyl alcohol, hydroxyethyl acrylate or hydroxy ethyl methacrylate to the castor oil to form a mixture; and (c) heating this mixture at 260°-275° C. for 3 to 4 hours to form a graft polyol.
Claim 24
Dependent Claim
57 words
A process for preparing a graft polyol which comprises: (a) placing castor oil in a pressurized reactor, (b) adding cyclopentadiene or dicyclopentadiene, and allyl alcohol, hydroxyethyl acrylate or hydroxy ethyl methacrylate to the castor oil to form a mixture; and (c) heating this mixture at 260°-275° C. for 3 to 4 hours to form a graft polyol.
Claim 25
Dependent Claim
28 words
The process according to claim 19 wherein the castor oil is preheated between 50° to 150° C. with nitrogen sparging, and/or agitation to remove air from the reactor.
Claim 26
Dependent Claim
28 words
The process according to claim 19 wherein the castor oil is preheated between 250° to 275° C. with nitrogen sparging, and/or agitation to remove air from the reactor.
Claim 27
Dependent Claim
33 words
The process according to claim 19 wherein the cyclopentadiene or dicyclopentadiene, and allyl alcohol, hydroxyethyl acrylate, or hydroxy ethyl methacrylate are added individually or jointly to the castor oil by aliquots or continuously.
Claim 28
Dependent Claim
13 words
The graft polyol liquid reaction product produced by the process of claim 9.
Claim 29
Dependent Claim
13 words
The graft polyol liquid reaction product produced by the process of claim 13.
Claim 30
Dependent Claim
63 words
A graft polyol comprising the liquid reaction product of: (a) about 50 to 90 parts by weight of at least one vegetable oil; (b) about 5 to 40 parts by weight of at least one liquid cyclopentadienyl compound; and (c) about 1 to 25 parts by weight of at least one of a monoester of acrylic, methacrylic, or crotonic acid and a diol.
Claim 31
Dependent Claim
63 words
A graft polyol comprising the liquid reaction product of: (a) about 50 to 90 parts by weight of at least one vegetable oil; (b) about 5 to 40 parts by weight of at least one liquid cyclopentadienyl compound; and (c) about 1 to 25 parts by weight of at least one of a monoester of acrylic, methacrylic, or crotonic acid and a diol.
Claim 32
Dependent Claim
40 words
A graft polyol comprising the liquid reaction product of: (a) at least one vegetable oil; (b) at least one liquid cyclopentadienyl compound; and (c) at least one of a monoester of acrylic, or methacrylic, or crotonic acid and a diol.
Claim 33
Dependent Claim
40 words
A graft polyol comprising the liquid reaction product of: (a) at least one vegetable oil; (b) at least one liquid cyclopentadienyl compound; and (c) at least one of a monoester of acrylic, or methacrylic, or crotonic acid and a diol.
Claim 34
Dependent Claim
30 words
The graft polyol of claim 26 wherein the vegetable oil is chinawood oil, soybean oil, dehydrated castor oil, sunflower oil, cottom oil, safflower oil, perilla oil or a synthetic triglyceride.
Claim 35
Dependent Claim
71 words
The graft polyol liquid reaction product of claim 1 wherein the fatty carbon compound is ethylene glycol monoricinoleate; butane diol diricinoleate; an alcohol having eight or more carbon atoms and one ethylenic double bond; a polyol mixture produced by ethoxylation of dimer and trimer fatty acids; or an unsaturated hydroxy fatty acid having from eight to eighteen carbon atoms, at least one ethylenic double bond, and at least one hyroxyl group.
Claim 36
Dependent Claim
13 words
The graft polyol liquid reaction product produced by the process of claim 19.
Claim 37
Dependent Claim
72 words
A process for preparing a graft polyol liquid reaction product which comprises: (a) placing (i) at least one vegetable oil; (ii) at least one liquid cyclopentadienyl compound, and (iii) at least one of a monoester of acrylic, methacrylic, or crotonic acid and a diol in a pressurized reactor to form a mixture; and (b) heating this mixture at 250°-275° C. for a sufficient time to form a graft polyol liquid reaction product.
Claim 38
Dependent Claim
72 words
A process for preparing a graft polyol liquid reaction product which comprises: (a) placing (i) at least one vegetable oil; (ii) at least one liquid cyclopentadienyl compound, and (iii) at least one of a monoester of acrylic, methacrylic, or crotonic acid and a diol in a pressurized reactor to form a mixture; and (b) heating this mixture at 250°-275° C. for a sufficient time to form a graft polyol liquid reaction product.
Claim 39
Dependent Claim
13 words
The graft polyol liquid reaction product produced by the process of claim 30.
Claim 40
Dependent Claim
81 words
A process for preparing a graft polyol liquid reaction product which comprises: (a) placing at least one vegetable oil in a pressurized reactor; (b) preheating the vegetable oil (c) adding at least one liquid cyclopentadienyl compound and at least one of a monoester of acrylic, methacrylic, or crotonic acid and a diol to the preheated vegetable oil to form a mixture; and (d) heating this mixture at 250°-275° C. for a sufficient time to form a graft polyol liquid reaction product.
Claim 41
Dependent Claim
81 words
A process for preparing a graft polyol liquid reaction product which comprises: (a) placing at least one vegetable oil in a pressurized reactor; (b) preheating the vegetable oil (c) adding at least one liquid cyclopentadienyl compound and at least one of a monoester of acrylic, methacrylic, or crotonic acid and a diol to the preheated vegetable oil to form a mixture; and (d) heating this mixture at 250°-275° C. for a sufficient time to form a graft polyol liquid reaction product.
Claim 42
Dependent Claim
13 words
The graft polyol liquid reaction product produced by the process of claim 32.
Claim 43
Dependent Claim
42 words
The graft polyol according to claim 26 wherein the monoester is a monoester of acrylic, methacrylic or crotonic acid and ethylene glycol, propylene glycol, 1-4 butanediol, 1-6 hexanediol, 2,2 dimethyl-1,3-propanediol, 1-4 cyclohexane dimethanol, diethylene glycol, triethylene glycol, dipropylene glycol, or tripropylene glycol.
References Cited (Backward Citations)
US1982707A
Cited
US2192152A
Cited
US2397600A
Cited
US2398889A
Cited
US2387895A
Cited
US2390530A
Cited
US2392140A
Cited
US2443044A
Cited
US2601273A
Cited
US2822371A
Cited
US2837546A
Cited
US2792410A
Cited
US4064199A
Cited
US4256619A
Cited
US4330448A
Cited
US4339367A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-02-02 | 1990-08-04 | 1991-02-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-02-02 | 1994-08-04 | 1995-02-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-02-02 | 1998-08-04 | 1999-02-03 | $7700.00 | Window Closed / Lapsed |