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US4271289A
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Oxygen-curable mercapto-functional organic compound compositions catalyzed by metal carbonyl compounds and method of forming higher molecular weight products therefrom
Assignee: Dow Silicones Corp
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Filing: 1979-12-03
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Granted: 1981-06-02
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Expires: 1999-12-03
Abstract
Abstract Compositions which are stable in the absence of oxygen are formed by mixing the following substantially in the absence of oxygen (A) 100 parts by weight of at least one mercapto-functional organic compound which contains at least two mercapto groups per molecule; (B) 0 to 200 parts by weight of at least one filler; and (C) a catalytic amount of a metal carbonyl compound selected from the group consisting of Fe(CO) 5 , Fe 2 (CO) 9 , Fe 3 (CO) 12 , dicyclopentadienyldiiron tetracarbonyl, butadieneiron tricarbonyl, cyclohexadieneiron tricarbonyl, Ni(CO) 4 , dicyclopentadienyldinickel dicarbonyl, Mn 2 (CO) 10 , methylcyclopentadienylmanganese tricarbonyl and cyclopentadienylcobalt dicarbonyl, preferably from 0.1 to 6 parts by weight of an iron carbonyl compound per 100 parts by weight of (A). Such compositions polymerize or cure upon exposure to oxygen. When used in layers of up to 3 millimeters thick, these compositions polymerize or cure at room temperature in a reasonable amount of time to form higher molecular weight products which are useful as coatings, impregnants or elastomeric sealants.
Inventors
- 👤 Gary R. Homan
- 👤 Chi-Long Lee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 11:37
CPC Classifications
C; C08; C08L; C08L81/00; C08L81/04; C08G; C08G75/00; C08G75/14; C09; C09K; C09K3/00; C09K3/10; C09K3/1006; C09K3/1012
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
130 words
A composition, stable in the absence of oxygen, which consists essentially of a product obtained by mixing the following substantially in the absence of oxygen (A) 100 parts by weight of at least one mercapto-functional organic compound which contains an average of at least two mercapto groups per molecule and is free of silicon atoms, aliphatic unsaturation and radicals which are reactive with mercapto groups at room temperature; (B) 0 to 200 parts by weight of at least one filler; and (C) a catalytic amount of a metal carbonyl compound selected from the group consisting of Fe(CO) 5 , Fe 2 (CO) 9 , Fe 3 (CO) 12 , dicyclopentadienyldiiron tetracarbonyl, butadieneiron tricarbonyl, cyclohexadieneiron tricarbonyl, Ni(CO) 4 , dicyclopentadienyldinickel dicarbonyl, Mn 2 (CO) 10 , methylcyclopentadienylmanganese tricarbonyl and cyclopentadienylcobalt dicarbonyl.
Claim 2
Dependent Claim
130 words
A composition, stable in the absence of oxygen, which consists essentially of a product obtained by mixing the following substantially in the absence of oxygen (A) 100 parts by weight of at least one mercapto-functional organic compound which contains an average of at least two mercapto groups per molecule and is free of silicon atoms, aliphatic unsaturation and radicals which are reactive with mercapto groups at room temperature; (B) 0 to 200 parts by weight of at least one filler; and (C) a catalytic amount of a metal carbonyl compound selected from the group consisting of Fe(CO) 5 , Fe 2 (CO) 9 , Fe 3 (CO) 12 , dicyclopentadienyldiiron tetracarbonyl, butadieneiron tricarbonyl, cyclohexadieneiron tricarbonyl, Ni(CO) 4 , dicyclopentadienyldinickel dicarbonyl, Mn 2 (CO) 10 , methylcyclopentadienylmanganese tricarbonyl and cyclopentadienylcobalt dicarbonyl.
Claim 3
Dependent Claim
35 words
The composition as claimed in claim 1 wherein the catalytic amount of (C) is in the range of 0.1 to 6 parts by weight of metal carbonyl compound per 100 parts by weight of (A).
Claim 4
Dependent Claim
16 words
The composition as claimed in claim 2 wherein the metal carbonyl compound is Fe(CO) 5 .
Claim 5
Dependent Claim
120 words
The composition as claimed in claims 2 or 3 wherein (A) is at least one mercapto-functional organic compound selected from the group consisting of R 4 C(CH 2 OOCR 2 SH) 3 , C(CH 2 OOCR 2 SH) 4 , (HSR 2 COOCH 2 ) 3 CCH 2 OCH 2 C(CH 2 OOCR 2 SH) 3 , {HSR 2 COO(H)C}{CH 2 OOCR 2 SH} 2 and (HSR 2 COOCH 2 ) 3 CCH 2 OCH 2 C(CH 2 OOCR 2 SH) 2 CH 2 OCH 2 C(CH 2 OOCR 2 SH) 3 wherein R 2 is alkylene of 1 to 20 inclusive carbon atoms or phenylene and R 4 is an alkyl radical of 1 to 2 inclusive carbon atoms.
Claim 6
Dependent Claim
54 words
The composition as claimed in claim 4 having admixed therewith at least one organic polydisulfidepolymercaptan polymer having a molecular weight of approximately 500 to 12,000 which contains multiply recurring disulfide (--SS--) linkages between carbon atoms, exists as a liquid at 25° C. and contains an average of at least two mercapto groups per molecule.
Claim 7
Dependent Claim
19 words
A composition which consists essentially of a product formed upon exposure of the composition of claim 3 to oxygen.
Claim 8
Dependent Claim
20 words
A cured composition which consists essentially of a product formed upon exposure of the composition of claim 4 to oxygen.
Claim 9
Dependent Claim
20 words
A cured composition which consists essentially of a product formed upon exposure of the composition of claim 5 to oxygen.
Claim 10
Independent Claim
122 words
A method of forming a higher molecular weight product which consists essentially of the steps of (I) mixing (a) 100 parts by weight of at least one mercapto-functional organic compound which contains an average of at least two mercapto groups per molecule and is free of silicon atoms, aliphatic unsaturation and radicals which are reactive with mercapto groups at room temperature and (b) a catalytic amount of a metal carbonyl compound selected from the group consisting of Fe(CO) 5 , Fe 2 (CO) 9 , Fe 3 (CO) 12 , dicyclopentadienyldiiron tetracarbonyl, butadieneiron tricarbonyl, cyclohexadieneiron tricarbonyl, Ni(CO) 4 , dicyclopentadienyldinickel dicarbonyl, Mn 2 (CO) 10 , methylcyclopentadienylmanganese tricarbonyl and cyclopentadienylcobalt dicarbonyl, to form a mixture and (II) exposing said mixture to oxygen
Claim 11
Independent Claim
122 words
A method of forming a higher molecular weight product which consists essentially of the steps of (I) mixing (a) 100 parts by weight of at least one mercapto-functional organic compound which contains an average of at least two mercapto groups per molecule and is free of silicon atoms, aliphatic unsaturation and radicals which are reactive with mercapto groups at room temperature and (b) a catalytic amount of a metal carbonyl compound selected from the group consisting of Fe(CO) 5 , Fe 2 (CO) 9 , Fe 3 (CO) 12 , dicyclopentadienyldiiron tetracarbonyl, butadieneiron tricarbonyl, cyclohexadieneiron tricarbonyl, Ni(CO) 4 , dicyclopentadienyldinickel dicarbonyl, Mn 2 (CO) 10 , methylcyclopentadienylmanganese tricarbonyl and cyclopentadienylcobalt dicarbonyl, to form a mixture and (II) exposing said mixture to oxygen
Claim 12
Dependent Claim
43 words
The method as claimed in claim 9 wherein the amount of metal carbonyl compound present is in the range of from 0.1 to 6 parts by weight per 100 parts by weight of (I)(a) and the metal carbonyl compound is Fe(CO) 5 .
Claim 13
Dependent Claim
32 words
The method as claimed in claim 9 wherein the mixture of (I) additionally contains up to 200 parts by weight of at least one filler per 100 parts by weight of (I)(a).
Claim 14
Dependent Claim
20 words
A composition which consists essentially of the higher molecular weight product obtained in accordance with the method of claim 9.
Claim 15
Dependent Claim
20 words
A composition which consists essentially of the higher molecular weight product obtained in accordance with the method of claim 10.
Claim 16
Dependent Claim
20 words
A composition which consists essentially of the higher molecular weight product obtained in accordance with the method of claim 11.
Claim 17
Dependent Claim
77 words
The composition as claimed in claim 1 wherein the metal carbonyl compound is selected from the group consisting of Fe(CO) 5 , Fe 2 (CO) 9 , Fe 3 (CO) 12 , dicyclopentadienyldiiron tetracarbonyl, butadieneiron tricarbonyl and cyclohexadieneiron tricarbonyl, the amount of said metal carbonyl compound present being such that the ratio of total moles of mercapto groups present in (A) to total moles of iron atoms present in said metal carbonyl compound is greater than one.
Claim 18
Dependent Claim
76 words
The composition as claimed in claim 1 wherein the metal carbonyl compound is Fe(CO) 5 , the catalytic amount of Fe(CO) 5 is in a range of 0.1 to 6 parts by weight per 100 parts by weight of (A) and the amount of Fe(CO) 5 present is such that the ratio of total moles of mercapto groups present in (A) to total moles of iron atoms present in the Fe(CO) 5 is greater than one.
Claim 19
Dependent Claim
13 words
The composition as claimed in claim 1 which contains at least one filler.
Claim 20
Dependent Claim
13 words
The composition as claimed in claim 2 which contains at least one filler.
Claim 21
Dependent Claim
13 words
The composition as claimed in claim 3 which contains at least one filler.
Claim 22
Dependent Claim
13 words
The composition as claimed in claim 6 which contains at least one filler.
Claim 23
Dependent Claim
13 words
The composition as claimed in claim 15 which contains at least one filler.
Claim 24
Dependent Claim
13 words
The composition as claimed in claim 16 which contains at least one filler.
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) | 1984-06-01 | 1984-12-01 | 1985-06-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-01 | 1988-12-01 | 1989-06-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-01 | 1992-12-01 | 1993-06-02 | $7700.00 | Window Closed / Lapsed |