Patent US4477366A successfully refreshed from Google Patents.
US4477366A
Expired / Lapsed
US
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Silicone surfactant/organofunctional polysiloxane internal mold release agents
Assignee: HUNTSMAN ICI HOLDINGS LLC
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Filing: 1983-05-23
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Granted: 1984-10-16
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Expires: 2003-05-23
Abstract
Abstract Blends of silicone surfactants substantially free of isocyanate reactivity and certain polysiloxane compounds having pendant organic chains which have at least one isocyanate reactive functional group are useful as internal mold release agents. These blends form stable dispersions in liquid polyisocyanates for use in reaction injection molding techniques.
Inventors
- 👤 John R. Robertson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 09:02
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/708; B; B29; B29C; B29C33/00; B29C33/56; B29C33/60; B29C33/62; B29C33/64; C08G18/28; C08G18/40; C08G18/61; B29C67/00; B29C67/24; B29C67/246; B29K; B29K2075/00; C08G2120/00; C08G2125/00
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
365 words
A liquid for use in preparing reaction injected molded polyurethane or polyurea resins having improved mold release properties which comprises 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, and from 1-25 percent based on the weight of said polysiloxane mold release agent of a liquid silicone surfactant substantially free of isocyanate reactivity.
Claim 2
Dependent Claim
365 words
A liquid for use in preparing reaction injected molded polyurethane or polyurea resins having improved mold release properties which comprises 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, and from 1-25 percent based on the weight of said polysiloxane mold release agent of a liquid silicone surfactant substantially free of isocyanate reactivity.
Claim 3
Dependent Claim
105 words
A composition of claim 1 wherein said silicone surfactant has the general formula: (CH.sub.3).sub.3 Si[OSi(CH.sub.3).sub.2 ].sub.x [CH.sub.3 R.sup.+ SiO].sub.y [CH.sub.3 R.sup.* SiO].sub.z OSi(CH.sub.3).sub.3 where the value of x, y or z vary from 10-1000 and R + and R * may be the same or different and are selected from alkyl radicals such as polyalkyl ether or alkoxyether group or grafted methoxy, ethoxy, ethylene, styrene, trifluoropropene, allyltetrahydrofurfurylether, allyloxyethyl acetate, acrolein diethylacetal, allylcyanide, allyloxyethyl cyanide, allylmorpholine, and allylchloride, where the sum of the total formula weight for R + and R * ranges from 800-40,000 and the polysiloxane block ranges from 15-70% of the molecular weight.
Claim 4
Dependent Claim
66 words
A composition of claim 1 wherein said surfactant has the general formula: Me.sub.3 SiO(Me.sub.2 SiO).sub.x [Z'O(CHMeCH.sub.2 O).sub.m (C.sub.2 H.sub.4 O).sub.n ZSi(Me)O ].sub.4 SiMe.sub.3 where Me=CH 3 ; x is 42-125; y is 3-15; m is 15-30; n is 10-30; Z' is selected from the group consisting of alkyl, aryl and aralkyl radicals; and Z is selected from the group consisting of alkylene, arylene, and aralkylene radicals.
Claim 5
Dependent Claim
30 words
A composition of claim 3 wherein x is 65.6, y is 6.1, Z' is --CH 3 , Z is --C 3 H 6 --, m is 23, n is 20.2.
Claim 6
Dependent Claim
14 words
A composition of claim 1 wherein said polysiloxane has a molecular weight of 2000-15,000.
Claim 7
Dependent Claim
14 words
A composition of claim 1 wherein said polysiloxane has a molecular weight of 4000-8000.
Claim 8
Dependent Claim
11 words
A composition of claim 1 having a viscosity of 1-100,000 centistokes.
Claim 9
Dependent Claim
28 words
A composition 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 10
Dependent Claim
56 words
A composition 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, --R'"--SCH 2 CO 2 H 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 11
Dependent Claim
23 words
A composition 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 12
Dependent Claim
15 words
A composition of claim 10 having a hydroxyl equivalent weight of between 500 and 2,000.
Claim 13
Dependent Claim
22 words
A composition of claim 10 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 14
Dependent Claim
23 words
A composition 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 15
Dependent Claim
22 words
A composition 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 16
Dependent Claim
22 words
A composition 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 17
Dependent Claim
22 words
A composition 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 18
Dependent Claim
19 words
A composition of claim 1 wherein R is --CH 2 CH 2 CH 2 SCH 2 CH 2 OH.
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
US4071483A
Cited
US3980688A
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
US4419261A
Cited
US4331555A
Cited
US4330447A
Cited
US4379100A
Cited
US4355062A
Cited
US4427798A
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) | 1987-10-16 | 1988-04-16 | 1988-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-16 | 1992-04-16 | 1992-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-16 | 1996-04-16 | 1996-10-16 | $7700.00 | Window Closed / Lapsed |