US4515724A
Expired / Lapsed
US
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Boron alkyl compounds and processes for their manufacture and use
Assignee: Henkel AG and Co KGaA
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Filing: 1982-08-30
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Granted: 1985-05-07
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Expires: 2002-08-30
Abstract
Abstract Novel boron alkyl compounds which are esters of a fatty acid or a fatty alcohol and which have at least one boryl radical or organoboron radical attached thereto. These boron alkyl compounds can be used to harden monomer adhesives, and are stable and active even when exposed to air.
Inventors
- 👤 Wolfgang Ritter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 07:37
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/55; A; A61; A61K; A61K6/00; A61K6/60; A61K6/61; A61L; A61L27/00; A61L27/14; A61L27/16; C07; C07F; C07F5/00; C07F5/02; C07F5/027; C09; C09J; C09J4/00
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
169 words
A boron alkyl compound comprising the addition product of an unsaturated ester, having double bonds of which about 30 to 100% are hydroborated with a boron compound; said ester being either (a) comprised within at least one naturally occurring unsaturated fat or oil or mixture thereof having about 12 to 22 carbon atoms, or (b) at least one synthetic reaction product of a C 12-22 hydroxy or non-hydroxy fatty acid or alcohol which has at least one olefinic double bond with a complementary polyfunctional alcohol or carboxylic acid containing from 2 to 10 carbon atoms in addition to any carboxyl radicals present; and said ester (a) or (b) having an iodine number between about 5 and 130; said boron compound being at least one borane or organoborane having at least one alkyl, cycloalkyl or aryl radical with from 1 to 25 carbon atoms; and wherein said boron alkyl compound has enhanced stability in the presence of air and is soluble in reaction systems containing monomers having polymerizable double bonds.
Claim 2
Dependent Claim
169 words
A boron alkyl compound comprising the addition product of an unsaturated ester, having double bonds of which about 30 to 100% are hydroborated with a boron compound; said ester being either (a) comprised within at least one naturally occurring unsaturated fat or oil or mixture thereof having about 12 to 22 carbon atoms, or (b) at least one synthetic reaction product of a C 12-22 hydroxy or non-hydroxy fatty acid or alcohol which has at least one olefinic double bond with a complementary polyfunctional alcohol or carboxylic acid containing from 2 to 10 carbon atoms in addition to any carboxyl radicals present; and said ester (a) or (b) having an iodine number between about 5 and 130; said boron compound being at least one borane or organoborane having at least one alkyl, cycloalkyl or aryl radical with from 1 to 25 carbon atoms; and wherein said boron alkyl compound has enhanced stability in the presence of air and is soluble in reaction systems containing monomers having polymerizable double bonds.
Claim 3
Dependent Claim
23 words
The boron alkyl compound of claim 1 wherein said ester is comprised within the at least one naturally occurring unsaturated fat or oil.
Claim 4
Dependent Claim
44 words
The boron alkyl compound of claim 2 wherein said ester is comprised within: coconut oil, palm kernel oil, beef tallow, palm oil, lard, sperm oil, castor oil, peanut oil, rapeseed oil, cottonseed oil, soybean oil, herring oil, sunflower oil, linseed oil, or mixtures thereof.
Claim 5
Dependent Claim
17 words
The boron alkyl compound of claim 1, 2, or 3 wherein said boron compound is the organoborane.
Claim 6
Dependent Claim
18 words
The boron alkyl compound of claim 4 wherein said organoborane radicals have from 1 to 15 carbon atoms.
Claim 7
Dependent Claim
21 words
The boron alkyl compound of claim 4 wherein said at least one radical and the boron atom form a ring system.
Claim 8
Dependent Claim
19 words
The boron alkyl compound of claim 4 wherein said organoborane compound is: 9-borabicyclo[3.3.1]nonane; diisopinocampheylborane; dicyclohexylborane; 2,3-dimethyl-2-butylborane; 3,5-dimethylborinane; or diisoamylborane.
Claim 9
Dependent Claim
13 words
The boron alkyl compound of claim 4 wherein said organoborane compound is 9-borabicyclo[3.3.1]nonane.
Claim 10
Dependent Claim
18 words
The boron alkyl compound of claim 1, 2, or 3 wherein said boron compound is a.BH 3 .
Claim 11
Dependent Claim
59 words
The boron alkyl compound of claim 1 wherein said ester is the at least one synthetic reaction product of a C 12-22 hydroxy or non-hydroxy fatty acid or alcohol which has at least one olefinic double bond with a complementary polyfunctional alcohol or carboxylic acid containing from 2 to 10 carbon atoms in addition to any carboxyl radicals present.
Claim 12
Dependent Claim
20 words
The boron alkyl compound of claim 10 wherein said fatty acid or alcohol has from 14 to 22 carbon atoms.
Claim 13
Dependent Claim
32 words
The boron alkyl compound of claim 10 wherein said fatty acid or alcohol is dodecenoic, tetradecenoic, hexadecenoic, octadecenoic, eicosenoic, docosenoic, 12-hydroxy-octadecenoic, octadecadienoic, octadecatrienoic, eicosatetraenoic, or docasapentaenoic acid or alcohol or mixtures thereof.
Claim 14
Dependent Claim
38 words
The boron alkyl compound of claim 10, 11, or 12 wherein said polyfunctional compound is a polyfunctional alcohol having from 2 to 6 hydroxyl radicals, a polyfunctional acid having from 2 to 6 carboxyl radicals, or mixtures thereof.
Claim 15
Dependent Claim
24 words
The boron alkyl compound of claim 13 wherein said polyfunctional compound has 2 to 6 carbon atoms in addition to any carboxyl radicals present.
Claim 16
Dependent Claim
43 words
The boron alkyl compound of claim 10, 11, or 12 wherein said polyfunctional compound is a lower glycol, a C 4 glycol with terminal and/or inner hydroxyl groups, the corresponding C 5 or C 6 glycols, the corresponding glycollic acids, or mixtures thereof.
Claim 17
Dependent Claim
15 words
The boron alkyl compound of claim 15 wherein the polyfunctional compound is glycerol or pentaerythritol.
Claim 18
Dependent Claim
16 words
The boron alkyl compound of claim 14 wherein said organoborane compound is a .BH 3 .
Claim 19
Dependent Claim
26 words
The boron alkyl compound of claim 14 wherein said boron compound is an organoborane and wherein said organoborane radicals have from 1 to 15 carbon atoms.
Claim 20
Dependent Claim
19 words
The boron alkyl compound of claim 18 wherein said organoborane compound is: 9-borabicyclo[3.3.1]nonane; diisopinocampheylborane; dicyclohexylborane; 2,3-dimethyl-2-butylborane; 3,5-dimethylborinane; or diisoamylborane.
Claim 21
Dependent Claim
13 words
The boron alkyl compound of claim 18 wherein said organoborane compound is 9-borabicyclo[3.3.1]nonane.
Claim 22
Dependent Claim
51 words
The boron alkyl compound of claim 1 wherein said ester is (a) and at least one of: solid palm oil, liquid palm oil, oleic acid methyl ester, peanut oil, a C 18' .C 18" fatty acid methylester mixture, linseed oil, peanut oil, soybean oil, 1,3-propylene glycoldioleate, pentaerythritetetraoleate, or synthetic jojoba oil.
Claim 23
Dependent Claim
13 words
The boron alkyl compound of claim 21 wherein said boron compound is 9-borabicyclo[3.3.1]nonane.
Claim 24
Dependent Claim
19 words
The boron alkyl compound of claim 22 wherein the degree of hydroboration of the double bonds is about 100%.
Claim 25
Dependent Claim
48 words
The boron alkyl compound of claim 1 wherein said ester is at least one of peanut oil or a C 18' .C 18" fatty acid methylester mixture, wherein said boron compound is .BH 3 , and wherein the degree of hydroboration of the double bonds is about 100%.
Claim 26
Dependent Claim
21 words
The boron alkyl compound of claim 1 wherein the degree of hydroboration of the double bonds is about 50 to 100%.
Claim 27
Dependent Claim
21 words
The boron alkyl compound of claim 1 wherein the degree of hydroboration of the double bonds is about 70 to 100%.
Claim 28
Dependent Claim
20 words
The boron alkyl compound of claim 4 wherein the degree of hydroboration of the double bonds is at least 80%.
Claim 29
Dependent Claim
20 words
The boron alkyl compound of claim 4 wherein the degree of hydroboration of the double bonds is at least 90%.
Claim 30
Dependent Claim
20 words
The boron alkyl compound of claim 18 wherein the degree of hydroboration of the double bonds is at least 80%.
Claim 31
Dependent Claim
20 words
The boron alkyl compound of claim 18 wherein the degree of hydroboration of the double bonds is at least 90%.
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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) | 1988-05-06 | 1988-11-05 | 1989-05-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-05-06 | 1992-11-05 | 1993-05-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-05-06 | 1996-11-05 | 1997-05-07 | $7700.00 | Window Closed / Lapsed |