Patent US5352566A successfully refreshed from Google Patents.
US4546154A
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Process for forming mold releasable polyurethane, polyurea and polyureaurethane resins using isocyanate reactive polysiloxanes as internal mold release agents
Assignee: HUNTSMAN ICI HOLDINGS LLC
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Filing: 1983-05-23
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Granted: 1985-10-08
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Expires: 2003-05-23
Abstract
Abstract Polyurethane, polyurea and polyureaurethane resins having improved mold release properties are made by including with the reactive ingredients certain internal mold release agents which are polysiloxane polymers having pendant organic groups which contain at least one hydroxyl, amino or mercapto group.
Inventors
- 👤 John R. Robertson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 05:12
CPC Classifications
B; B29; B29C; B29C33/00; B29C33/56; B29C33/60; B29C33/62; B29C33/64; C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/61; B29C67/00; B29C67/24; B29C67/246; B29K; B29K2075/00; B29K2083/00; C08G2125/00; Y; Y10; Y10S; Y10S264/00; Y10S264/83
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
376 words
In a process for preparing resins by the reaction injection molding technique which comprises the impingement mixing of liquid organic polyisocyanates with isocyanate reactive ingredients selected from the group consisting of polyols, polyamines, polyolamines and catalysts the improvement which consists of dispersing therewith from 0.5-15 percent by weight based on the total reaction mix of a polysiloxane mold release agent which consists essentially of 0.5-20 mol percent of R a R' b SiO.sub.[4-(a+b)]/2 units and from 80-99.5 mol percent of R" c SiO.sub.(4-c)/2 units where R is an isocyanate reactive organic radical, a has an average value of from 1-3, R' and R" are both non-isocyanate reactive organic radicals, b has an average value of 0-2, a+b is from 1-3, and c has an average value of from 1-3, wherein the ratio of the total molecular weight to the total number of isocyanate reactive functional groups in the molecule ranges from 100-3500, the combined formula weights of all isocyanate reactive organic radicals, R do not exceed 40% of the total molecular weight of said polysiloxane mold release agent, the combined formula weights of all non-isocyanate reactive radicals, R'+R" together do not exceed 40% of the total molecular weight of said polysiloxane mold release additive, the combined formula weights of all the organic radicals R+R'+R" in the molecule together do not exceed 60% of the total molecular weight of the molecule, said polysiloxane mold release agent contains an average of at least two isocyanate reactive functional groups per molecule, at least two of the isocyanate reactive functional groups in each molecule are located on separate organic radicals, R, attached independently to different silicon atoms in said polysiloxane, said isocyanate reactive functional groups (R) are selected from the group consisting of alcohols, phenols, thiols, primary or secondary aromatic amines, which contain no oxygen, and not more than one nitrogen, atoms attached directly to, in conjugation with, or incorporated within, the aromatic ring nucleous, and secondary aliphatic amines wherein at least one of the alkyl carbon atoms, bonded directly to the nitrogen atom, is not a primary carbon atom and carboxylic acids, the molecular weight of said polysiloxane mold release agent ranges from 1000 and 30,000, and said polysiloxane mold release agent being substantially insoluble in said liquid polyisocyanate.
Claim 2
Dependent Claim
376 words
In a process for preparing resins by the reaction injection molding technique which comprises the impingement mixing of liquid organic polyisocyanates with isocyanate reactive ingredients selected from the group consisting of polyols, polyamines, polyolamines and catalysts the improvement which consists of dispersing therewith from 0.5-15 percent by weight based on the total reaction mix of a polysiloxane mold release agent which consists essentially of 0.5-20 mol percent of R a R' b SiO.sub.[4-(a+b)]/2 units and from 80-99.5 mol percent of R" c SiO.sub.(4-c)/2 units where R is an isocyanate reactive organic radical, a has an average value of from 1-3, R' and R" are both non-isocyanate reactive organic radicals, b has an average value of 0-2, a+b is from 1-3, and c has an average value of from 1-3, wherein the ratio of the total molecular weight to the total number of isocyanate reactive functional groups in the molecule ranges from 100-3500, the combined formula weights of all isocyanate reactive organic radicals, R do not exceed 40% of the total molecular weight of said polysiloxane mold release agent, the combined formula weights of all non-isocyanate reactive radicals, R'+R" together do not exceed 40% of the total molecular weight of said polysiloxane mold release additive, the combined formula weights of all the organic radicals R+R'+R" in the molecule together do not exceed 60% of the total molecular weight of the molecule, said polysiloxane mold release agent contains an average of at least two isocyanate reactive functional groups per molecule, at least two of the isocyanate reactive functional groups in each molecule are located on separate organic radicals, R, attached independently to different silicon atoms in said polysiloxane, said isocyanate reactive functional groups (R) are selected from the group consisting of alcohols, phenols, thiols, primary or secondary aromatic amines, which contain no oxygen, and not more than one nitrogen, atoms attached directly to, in conjugation with, or incorporated within, the aromatic ring nucleous, and secondary aliphatic amines wherein at least one of the alkyl carbon atoms, bonded directly to the nitrogen atom, is not a primary carbon atom and carboxylic acids, the molecular weight of said polysiloxane mold release agent ranges from 1000 and 30,000, and said polysiloxane mold release agent being substantially insoluble in said liquid polyisocyanate.
Claim 3
Dependent Claim
14 words
A process of claim 1 wherein said polysiloxane has a molecular weight of 2000-15,000.
Claim 4
Dependent Claim
14 words
A process of claim 1 wherein said polysiloxane has a molecular weight of 4000-8000.
Claim 5
Dependent Claim
14 words
A process of claim 1 wherein said polysiloxane has a viscosity of 1-100,000 centistokes.
Claim 6
Dependent Claim
28 words
A process of claim 1 wherein R, R', and R" are organic radicals attached to silicon by carbon to silicon bonds, by carbon-oxygen-silicon bonds, or by carbon-sulfur-silicon bonds.
Claim 7
Dependent Claim
51 words
A process of claim 1 wherein R is selected from the group consisting of R'"--OH, R'"--CHOHCH 2 OH, R'"--CHOHCH 3 , R'"--SH, R'"--CH 2 SH, wherein R'" is a divalent linking group composed of carbon and hydrogen; carbon, hydrogen, and oxygen; carbon, hydrogen, and sulfur; or carbon, hydrogen, oxygen, and sulfur.
Claim 8
Dependent Claim
23 words
A process of claim 1 wherein R is --CH 2 CH 2 CH 2 O--[CH 2 CH(CH 3 )O] n --H where n=1-5.
Claim 9
Dependent Claim
18 words
A process of claim 7 wherein said polysiloxane has a hydroxyl equivalent weight of between 500 and 2,000.
Claim 10
Dependent Claim
22 words
A process of claim 7 wherein said polysiloxane has the general formula: (CH.sub.3).sub.3 SiO[Si(CH.sub.3).sub.2 O].sub.66 [Si(CH.sub.3 (C.sub.3 H.sub.6 O(CH.sub.2 CH(CH.sub.3)O).sub.2.5 H)O].sub.3 Si(CH.sub.3).sub.3.
Claim 11
Dependent Claim
22 words
A process of claim 1 wherein said polysiloxane has the general formula: (CH.sub.3).sub.3 SiO[Si(CH.sub.3).sub.2 O].sub.63 [SiCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CHOHCH.sub.2 OH)(CH.sub.3)O].sub.7 Si(CH.sub.3).sub.3.
Claim 12
Dependent Claim
22 words
A process of claim 1 wherein said polysiloxane has the general formula: (CH.sub.3).sub.3 SiO[Si(CH.sub.3).sub.2 O].sub.65 [SiCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CHOHCH.sub.2 OH)(CH.sub.3)O].sub.5 Si(CH.sub.3).sub.3.
Claim 13
Dependent Claim
22 words
A process of claim 1 wherein said polysiloxane has the general formula: (CH.sub.3).sub.3 SiO[Si(CH.sub.3).sub.2 O].sub.56 [SiCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CHOHCH.sub.2 OH)(CH.sub.3)O].sub.14 Si(CH.sub.3).sub.3.
Claim 14
Dependent Claim
22 words
A process of claim 1 wherein said polysiloxane has the general formula: (CH.sub.3).sub.3 SiO[Si(CH.sub.3).sub.2 O].sub.134 [SiCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.2 CHOHCH.sub.2 OH)(CH.sub.3)O].sub.16 Si(CH.sub.3).sub.3.
Claim 15
Dependent Claim
17 words
A process of claim 1 wherein R is CH 2 CH 2 SCH 2 CN 2 OH.
Claim 16
Dependent Claim
13 words
A process of claim 1 wherein said organic polyisocyanate is an aromatic polyisocyanate.
Claim 17
Dependent Claim
34 words
A process of claim 15 wherein said aromatic polyisocyanate is selected from the group consisting of the isomers of toluene diisocyanate, the isomers of diphenylmethane diisocyanate, and the isomers of methylene bridged diphenylmethane diisocyanate.
Claim 18
Dependent Claim
23 words
A process of claim 15 wherein said diphenylmethane diisocyanate contains minor amounts of uretonimine, carbodiimide and low molecular weight polyol modified diphenylmethane diisocyanate.
Claim 19
Dependent Claim
11 words
A fully cured resin made by the process of claim 1.
References Cited (Backward Citations)
US3097176A
Cited
US3194773A
Cited
US3397158A
Cited
US3194770A
Cited
US3202620A
Cited
US3178490A
Cited
US3373122A
Cited
US3505377A
Cited
US3476933A
Cited
US3579471A
Cited
US3632557A
Cited
US3718613A
Cited
US3703489A
Cited
US3933756A
Cited
US3879433A
Cited
US4254228A
Cited
US4033912A
Cited
US3954824A
Cited
US3980688A
Cited
US4071483A
Cited
US3979344A
Cited
US3941733A
Cited
US4052495A
Cited
US4092275A
Cited
US4111861A
Cited
US4220727A
Cited
US4076695A
Cited
US4242467A
Cited
US4355171A
Cited
US4369300A
Cited
US4336358A
Cited
US4378389A
Cited
US4350777A
Cited
DE3012126A1
Cited
US4331555A
Cited
US4330447A
Cited
US4379100A
Cited
US4355062A
Cited
US4369268A
Cited
US4348510A
Cited
US4367291A
Cited
US4345053A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-10-07 | 1989-04-08 | 1989-10-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-07 | 1993-04-08 | 1993-10-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-07 | 1997-04-08 | 1997-10-08 | $7700.00 | Window Closed / Lapsed |