US4543369A
Expired / Lapsed
US
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Alkoxylated polyester polyols and polyurethanes made therefrom
Assignee: Henkel Corp
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Filing: 1984-10-26
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Granted: 1985-09-24
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Expires: 2004-10-26
Abstract
Abstract Alkoxylated polyester polyols useful in the manufacture of polyurethanes are disclosed. For example, 9(10)-methylhydroxymethyloctadecanoate can be reacted with bishydroxymethyltricyclodecane to prepare a polyester polyol which can be ethoxylated to prepare an alkoxylated polyester polyol. The resulting polyester polyol can be reacted with a diisocyanate, such as a modified diphenylmethane diisocyanate, to prepare a urethane elastomer.
Inventors
- 👤 Dwight E. Peerman
- 👤 Edgar R. Rogier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 13:22
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/36; C08G18/40; C08G18/42; C08G18/4266; C08G18/4283; C08G18/48; C08G18/4891; C08G18/67; C08G18/68; C08G18/683; C08G18/686
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
193 words
Urethane linked reaction products of (a) at least one alkoxylated polyester polyol formed by reacting (i) at least one non-gelled polyester polyol of the formula: R--O--A--H].sub.p where R is a polyol residue; p is an integer from 2 to 6; and, A may be the same or different and is selected from the group consisting of A 1 , A 2 , and A 3 , and combinations of A 1 , A 2 and A 3 , where ##STR12## where m, n, p, q, r, α, β and γ are integers and where m>3 n≧0 and m+n is from 11 to 19 q>3 r≧0 s≧0 and q+r+s is from 10 to 18 α is from 0 to 10 β is from 0 to 10 and γ is from 1 to 10, except that all α's, β's and γ's in any given compound are not all zero; with (ii) at least one alkylene oxide in a ratio of moles of alkylene oxide per equivalents of hydroxyl in the polyester polyol from about 0.5:1 to 5:1; and (b) from about 80% to about 120% on a hydroxyl-isocyanate equivalent basis of at least one polyisocyanate.
Claim 2
Dependent Claim
193 words
Urethane linked reaction products of (a) at least one alkoxylated polyester polyol formed by reacting (i) at least one non-gelled polyester polyol of the formula: R--O--A--H].sub.p where R is a polyol residue; p is an integer from 2 to 6; and, A may be the same or different and is selected from the group consisting of A 1 , A 2 , and A 3 , and combinations of A 1 , A 2 and A 3 , where ##STR12## where m, n, p, q, r, α, β and γ are integers and where m>3 n≧0 and m+n is from 11 to 19 q>3 r≧0 s≧0 and q+r+s is from 10 to 18 α is from 0 to 10 β is from 0 to 10 and γ is from 1 to 10, except that all α's, β's and γ's in any given compound are not all zero; with (ii) at least one alkylene oxide in a ratio of moles of alkylene oxide per equivalents of hydroxyl in the polyester polyol from about 0.5:1 to 5:1; and (b) from about 80% to about 120% on a hydroxyl-isocyanate equivalent basis of at least one polyisocyanate.
Claim 3
Dependent Claim
130 words
Urethane-linked reaction products of (a) at least one alkoxylated polyester polyol formed by reacting (i) at least one polyester polyol of the formula: ##STR13## where R 1 is a polyol residue; p is an integer from 2 to 6; α is an integer from 0 to 10 and may be the same or different in each bracketed moiety of the formula, except that all α's are not all zero; m and n are integers where m>3 n≧0 and m+n is from 11 to 19; and (ii) at least one alkylene oxide in a ratio of moles of alkylene oxide to equivalents of hydroxyl in said polyester polyol from about 0.5:1 to 5:1, and (b) from about 80% to about 120% on a hydroxyl-isocyanate equivalent basis of at least one polyisocyanate.
Claim 4
Dependent Claim
130 words
Urethane-linked reaction products of (a) at least one alkoxylated polyester polyol formed by reacting (i) at least one polyester polyol of the formula: ##STR13## where R 1 is a polyol residue; p is an integer from 2 to 6; α is an integer from 0 to 10 and may be the same or different in each bracketed moiety of the formula, except that all α's are not all zero; m and n are integers where m>3 n≧0 and m+n is from 11 to 19; and (ii) at least one alkylene oxide in a ratio of moles of alkylene oxide to equivalents of hydroxyl in said polyester polyol from about 0.5:1 to 5:1, and (b) from about 80% to about 120% on a hydroxyl-isocyanate equivalent basis of at least one polyisocyanate.
Claim 5
Dependent Claim
27 words
The compositions of claim 1 or 2, wherein in the formula for said polyester polyol, p is 2 and R or R 1 is a diol residue.
Claim 6
Dependent Claim
10 words
The compositions of claim 3, wherein the diol is 1,4-butanediol.
Claim 7
Dependent Claim
54 words
The compositions of claim 3, wherein the diol is ##STR14## wherein R 1 , R 2 , R 3 and R 4 have a total of from 30 to 38 carbon atoms and are each straight-chained alkyl groups having at least 5 carbon atoms, and wherein two of these alkyl groups have omega-hydroxyl substituents.
Claim 8
Dependent Claim
11 words
The compositions of claim 3, wherein the diol is ethylene glycol.
Claim 9
Dependent Claim
10 words
The compositions of claim 3, wherein the diol is neopentylglycol.
Claim 10
Dependent Claim
18 words
The compositions of claim 3, wherein the diol is a compound of the formula: ##STR15## and mixtures thereof.
Claim 11
Dependent Claim
14 words
The compositions of claim 8 wherein the tricyclo compound is 8,8(9,9)-bis(hydroxymethyl)tricyclo[5,2,1,0 2 ,6 ]dec-3-ene.
Claim 12
Dependent Claim
14 words
The compositions of claim 8 wherein the tricyclo compound is 8,8-bis(hydroxymethyl)tricyclo[5,2,1,0 2 ,6 ]decane.
Claim 13
Dependent Claim
36 words
The compositions of claim 3, wherein the diol is H(CH.sub.2).sub.h CH(CH.sub.2 OH)(CH.sub.2).sub.k CH.sub.2 OH wherein k is 3 or greater; and h plus k are non-zero integers the sum of which is from 12 through 20.
Claim 14
Dependent Claim
10 words
The compositions of claim 11 wherein the diol is 9(10)-hydroxymethyloctadecanol.
Claim 15
Dependent Claim
10 words
The compositions of claim 3, wherein the diol is 1,4-bishydroxymethylcyclohexane.
Claim 16
Dependent Claim
22 words
The compositions of claim 3, wherein the diol is a member selected from the group consisting of 3(4), 8(9)-(bishydroxymethyl)-tricyclo[5,2,1,0 2 ,6 ]decane.
Claim 17
Dependent Claim
16 words
The compositions of claim 1 or 2, wherein R or R 1 is a triol residue.
Claim 18
Dependent Claim
10 words
The compositions of claim 15, wherein the triol is trimethylolpropane.
Claim 19
Dependent Claim
16 words
The compositions of claim 1 or 2, wherein R or R 1 is a tetrol residue.
Claim 20
Dependent Claim
10 words
The compositions of claim 17, wherein the tetrol is pentaerythritol.
Claim 21
Dependent Claim
66 words
The compositions of claim 1 or 2, wherein R or R 1 is derived from a polyol of the formula: CH.sub.3 (CH.sub.2).sub.a [C(CH.sub.2 OH).sub.2 ].sub.b (CH.sub.2).sub.c C(CH.sub.2 OH).sub.2 (CH.sub.2).sub.d [C(CH.sub.2 OH).sub.2 ].sub.e (CH.sub.2).sub.f CH.sub.2 OH and mixtures thereof, wherein b and e are 0 and 1; a and f are 3 or greater; c and d are non-zero integers; and a+b+c+d+e+f is from 11 to 19.
Claim 22
Dependent Claim
32 words
The compositions of claim 19, wherein the polyol includes a diol of the formula: H(CH.sub.2).sub.h CH(CH.sub.2 OH)(CH.sub.2).sub.k CH.sub.2 OH wherein k is 3 or greater; and h+k is from 12 to 20.
Claim 23
Dependent Claim
10 words
The compositions of claim 19, wherein the polyol is 9,9(10,10)-bishydroxymethyloctadecanol.
Claim 24
Dependent Claim
108 words
The compositions of claim 1 or 2, wherein R and R 1 is a polyol residue derived from a polyol of the formula: ##STR16## and mixtures thereof wherein R 1 and R 2 are selected from the group consisting of hydrogen and methyl and mixtures thereof with the provision that one such member must be hydrogen; and R 3 and R 4 are hydrogen or hydroxymethyl provided that at least one of R 3 and R 4 must be hydroxymethyl; and further that x is an integer of from 3 through 6 and y is an integer from 6 through 9 and that the sum x+y is 12.
Claim 25
Dependent Claim
24 words
The compositions of claim 1 or 2, wherein the polyisocyanate is present at from about 95% to about 105% on a hydroxyl-isocyanate equivalent basis.
Claim 26
Dependent Claim
22 words
The compositions of claim 1 or 2, wherein the polyisocyanate is selected from the group consisting of diisocyanates, triisocyanates and mixtures thereof.
Claim 27
Dependent Claim
14 words
The compositions of claim 1 or 2, wherein the polyisocyanate is an aromatic isocyanate.
Claim 28
Dependent Claim
16 words
The compositions of claim 1 or 2, wherein the polyisocyanate is an aliphatic or cycloaliphatic isocyanate.
Claim 29
Dependent Claim
53 words
The compositions of claim 1 or 2, wherein the polyisocyanate is selected from the group consisting of toluene diisocyanate, xylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, the triisocyanate adduct of hexamethylene diisocyanate and water, trimethyl hexamethylene diisocyanate, diphenylmethane diisocyanate, aliphatic diisocyanates having 12 to 40 carbon atoms in the aliphatic moiety and mixtures thereof.
Claim 30
Dependent Claim
34 words
The compositions of claim 1 or 2, wherein said reaction product is formed from at least one of said alkoxylated polyester polyols, at least one of said polyisocyanates and at least one modifying polyol.
Claim 31
Dependent Claim
36 words
The compositions of claim 28, wherein said modifying polyol is selected from the group consisting of alkyl and cycloalkyl polyols, ester linked polyols, ether linked polyols, ether and ester linked polyols and hydroxy functional acrylic copolymers.
Claim 32
Dependent Claim
21 words
The compositions of claim 1 or 2, further comprising modifying agents selected from the group consisting of fillers, dyes and plasticizers.
Claim 33
Dependent Claim
20 words
The compositions of claim 1 or 2, wherein said reaction product is formed in the presence of a trimerization catalyst.
Claim 34
Dependent Claim
14 words
An elastomer formed from a urethane linked reaction product of claim 1 or 2.
Claim 35
Dependent Claim
15 words
A microcellular foam formed from a urethane linked reaction product of claim 1 or 2.
Claim 36
Dependent Claim
15 words
A protective coating formed from a urethane linked reaction product of claim 1 or 2.
Claim 37
Dependent Claim
14 words
An adhesive formed from a urethane linked reaction product of claim 1 or 2.
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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) | 1988-09-23 | 1989-03-25 | 1989-09-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-23 | 1993-03-25 | 1993-09-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-23 | 1997-03-25 | 1997-09-24 | $7700.00 | Window Closed / Lapsed |