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Matched Legal Cases: ['art 2', 'art 4', 'art 5', 'art 6', 'art 1', 'art 2', 'art 3', 'art 4', 'art 5', 'art 6', 'art 2', 'art 1', 'art 2', 'art 3', 'art 4', 'art 5', 'art 6']

Patent US5886125 - Crosslinkable copolymers comprising vinyl silane and vinyl esters of ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsA copolymer composition and coating comprising the copolymer composition containing a vinyl silane of the formula ##STR1## where R1 is an aryl or alkyl group having 1 to 10 carbon atoms and R2 is a hydrolysable group; and a vinyl ester of a branched fatty acid having the formula ##STR2## wherein R3,...http://www.google.com/patents/US5886125?utm_source=gb-gplus-sharePatent US5886125 - Crosslinkable copolymers comprising vinyl silane and vinyl esters of branched fatty acidAdvanced Patent SearchPublication numberUS5886125 APublication typeGrantApplication numberUS 08/805,546Publication dateMar 23, 1999Filing dateFeb 25, 1997Priority dateFeb 25, 1997Fee statusLapsedAlso published asCA2230166A1Publication number08805546, 805546, US 5886125 A, US 5886125A, US-A-5886125, US5886125 A, US5886125AInventorsJosef HuybrechtsOriginal AssigneeE. I. Du Pont De Nemours And CompanyExport CitationBiBTeX, EndNote, RefManPatent Citations (35), Non-Patent Citations (43), Referenced by (16), Classifications (27), Legal Events (5) External Links: USPTO, USPTO Assignment, EspacenetCrosslinkable copolymers comprising vinyl silane and vinyl esters of branched fatty acid
US 5886125 AAbstract
A copolymer composition and coating comprising the copolymer composition containing a vinyl silane of the formula ##STR1## where R1 is an aryl or alkyl group having 1 to 10 carbon atoms and R2 is a hydrolysable group; and
a vinyl ester of a branched fatty acid having the formula ##STR2## wherein R3, R4, R5 are hydrogen or alkyl groups with 1 to 12 carbon atoms and
wherein the total of R3, R4 and R5 contain at least 3 carbon atoms and
1. A crosslinkable copolymeric composition having a weight average molecular weight below about 40,000, a hydroxyl value from about 20 to 160, and an acid value below about 20, derived from A, B and optionally, C, wherein:A is 5 to 95% by weight of A, B and C of a vinyl silane having the formula: ##STR12## where R1 is an aryl or alkyl group having 1 to 10 carbon atoms and R2 is a hydrolysable group; B is 5 to 95% by weight of a vinyl ester of a branched fatty acid having the formula ##STR13## wherein R3, R4, R5 are hydrogen or alkyl groups with 1 to 12 carbon atoms and wherein the total of R3, R4 and R5 contain at least 3 carbon atoms; and C is 0 to 90% by weight of a different polymerizable olefinically unsaturated compound. 2. A composition according to claim 1 having a weight average molecular weight between about 1,500 to 10,000, a hydroxyl value from about 20 to 160, and an acid value below about 10.
5. A composition according to claim 1 wherein m=0 and R2 is methoxy or ethoxy.
This invention concerns a crosslinkable polymeric composition having a weight average molecular weight below about 40,000 and an acid value below about 20 mg KOH/gram derived from A, B and optionally C, wherein:
A is 5 to 95% by weight of A, B and C of a vinyl silane having the formula: ##STR3## where R1 is an aryl or alkyl group having 1 to 10 carbon atoms and R2 is a hydrolysable group;
B is 5 to 95% by weight of a vinyl ester of a branched fatty acid having the formula ##STR4## wherein R3, R4, R5 are hydrogen or alkyl groups with 1 to 12 carbon atoms and
wherein the total of R3, R4 and R5 contain at least 3 carbon atoms; and
Preferred vinyl silanes are those wherein m=0 and R2 is methoxy or ethoxy.
Preferred vinyl esters are those derived from branched fatty acids such as pivalic acid wherein R3, R4 and R5 are each methyl; versatic acid 9, 10 or 11 wherein the total number of carbon atoms in R3, R4 and R5 are 7 , 8, and 9, respectively. Most preferred branched fatty acids are versatic 9 and versatic 10.
Typical ultraviolet light stabilizers that are useful include benzophenones, triazoles, triazines, benzoates, hindered amines and mixtures thereof. The composition can also include conventional formulation additives such as flow control agents such as Resiflow� S (polybutylacrylate), BYK� 320 and 325 (high molecular weight polyacrylates), rheology control agents, such as fumed silica; water scavengers such as tetrasilicate, trimethyl orthoformate, triethyl orthoformate, and the like.
The coating composition can be applied by conventional techniques such as spraying, electrostatic spraying, dipping, brushing, flowcoating, and the like. The preferred techniques are spraying and electrostatic spraying. After application, the composition is typically baked at 100� to 150� C. for about 15 to 30 minutes to form a coating of about 0.1 to 3.0 mils thick. When the composition is used as a clearcoat, it is applied over the colorcoat which can be dried to a tack-free state and cured or preferably flash-dried for a short period before the clearcoat is applied. The colorcoat/clearcoat finish is then baked as mentioned above to provide a dried and cured finish.
R6 --O--CO--CH&#9552;CH--CO--O--R7 wherein R6 and R7 are the same or different and are selected from alkylene, cycloalkylene, aryl, aralkylene, and alkaryl, of up to about 20 carbon atoms, interrupted by or substituted by heteroatoms and/or hydroxyl groups. Examples of such reaction products are the following.
R6 ##STR9## Component (ii)
The coating composition further includes, particularly in conjunction with a polyol polymer, an additional crosslinking agent, for example, conventionally known monomeric or polymeric alkylated melamine formaldehyde resin that is partially or fully alkylated. One preferred crosslinking agent is methylated and butylated or isobutylated melamine formaldehyde resin that has a degree of polymerization of about 1 to 3. Generally, this melamine formaldehyde resin contains about 50% butylated groups or isobutylated groups and 50% methylated groups. Such crosslinking agents typically have a number average molecular weight of about 300 to 600 and a weight average molecular weight of about 500 to 1,500. Examples of commercially available resins are Cymel� 1168, Cymel� 1161, Cymel� 1158, Resimine� 4514 and Resimine� 354. Preferably, the crosslinking agent is used in the amount of about 5 to 50% by weight, based on the weight of the binder of the composition. Other contemplated crosslinking agents are urea formaldehyde, benzoquanamine formaldehyde and blocked polyisocyanates.
Compositions of this invention can be made by the same techniques as those used in the synthesis of acrylic resins and vinyl resins. An example of such synthetic technology comprises dissolving or dispersing the respective component monomers in an organic solvent and heating the solution in the presence of a radical polymerization initiator at a temperature of about 60 to 180� C. with constant stirring. The reaction time is generally about 1 to 10 hours. As the organic solvent, the same alcohol, ether, ester and hydrocarbon solvents as mentioned hereinbefore can be employed. In the case of a hydrocarbon solvent, it is preferably used in combination with a different type of solvent from the standpoint of solubility.
Among the organic solvents which can be used for the polymerization are those which have a boiling point of at least 50� C. and usually from 110� to 180� C. These include, for example, ketones such as methyl amyl ketone, esters such as hexyl acetate and heptyl acetate; glycol ethers and glycol esters such as propylene glycol monoethyl ether acetate and isobutyl isobutyrate.
Veova�/Vinyl Silane/Hydroxypropyl methacrylate (blend) Copolymer
A reactor equipped with a reflux condenser, stirrer, thermometer, nitrogen gas inlet and dropping funnel was charged with a first part consisting of 6 parts of Solvesso� 100 (aromatic solvent blend; Exxon) and 4 parts of n-butanol. This was heated to 125� C. and part 2 consisting of 47.76 parts of Veova� 9 (Shell), vinyltrimethoxy silane (Silquest� A171, OSI), 7.96 parts of hydroxy propyl methacrylate, 5.4 parts of t-butyl peroxy isononanoate (Trigonox� 42S, AKZO) and 1.5 parts of Solvesso� 100 were added dropwise thereto from a dropping funnel over a 5 hour period.
After completin of the addition, a third part of Solvesso� 100 (1 part) was added as rinsing solvent and reactor contents held at reflux for 10 minutes. Afterwards, part 4 consisting of 0.6 parts of di-t-butyl peroxide (Trigonox� B) and 0.4 parts of Solvesso� 100 were added over 20 minutes followed by part 5 (0.5 Solvesso� 100) as rinsing step and the reactor contents were held at reflux for 2 hours. Part 6, consisting of 1 part Solvesso� 100 and 6.25 parts of n-butanol, were finally added to the reactor.
Test results: Solids 78.3% (1 hour dried at 105� C.)
Procedure of Example 1 was followed.
______________________________________    Ex 2   Ex 3     Ex 4    Ex 5  Ex 6______________________________________Part 1Solvesso � 100      6        6        6     10    10n-butanol  4        4        4     --    --Part 2Veova � 9      55.72    --       --    --    --Veova � 10      --       47.76    47.76 63.68 71.64Silquest � A171      15.92    23.88    23.88 15.92 7.962-Hydroxyethyl-      7.96     7.96     --    --    --methacrylateHydroxypropyl-      --       --       7.96  --    --methacrylateTrigonox � 21S      --       5.4      5.4   --    --Solvesso � 100      1.5      1.5      1.5   3.5   3.5VAZO � 67      5.4      --       --    --    --(DuPont)Trigonox � B      --       --       --    3.4   3.4Part 3Solvesso � 100      1        1        1     1     1Part 4Trigonox � B      0.5      0.6      0.6   0.6   0.6(AKZO)Solvesso � 100      0.5      0.4      0.4   0.4   0.4Part 5Solvesso � 100      0.5      0.5      0.5   0.5   0.5Part 6Solvesso � 100      1        1        1     7.25  7.25n-Butanol  --       6.25     6.25  --    --Test ResultsSolids     80.3     77.5     78.4  79.7  80.5Viscosity  &gt;Z6      X + 1/4  S     I     QAcid value 3.6      2.9      3.4   2     2.3Mn         3000     3200     2300  1100  1100Mw         24300    25700    7100  2200  2400______________________________________
Maleate Adduct; Component C
Part 2 consisting of 260 parts of Cardura� E10 (Shell) and 65 parts of Solvesso� 100 was then added to the reactor and the content was refluxed until the acid value was lower than 2.
Procedure 1 was repeated except that the initial reactor charge was 108 parts benzylalcohol, 98 parts Cardura� E10 and 51 parts of methyl isobutyl ketone.
First, 582 parts of the product of Procedure 1 was refluxed with 168 parts of methylhexahydrophthalic anhydride and 50 parts of Solvesso� 100 for 2 hours. Then, 260 parts of Cardura� E10 and 57 parts of Solvesso� 100 were added and the mixture refluxed until the acid value was below 2.
Procedure of Example 1 was repeated with following changes:
______________________________________    Ex 7   Ex 8     Ex 9    Ex 10 Ex 11______________________________________Part 1Maleate Procedure 1      --       9.95     --    --    --Maleate Procedure 2      19.80    --       --    --    --Maleate Procedure 3      --       --       39.8  --    --Solvesso � 100      6        5        --    7     10n-butanol  0.02     3        4     3     --Part 2Silquest � A1511      --       --       --    40    40.65Silquest � A1712      23.88    23.88    23.88 --    --Veova � 9      --       47.76    23.88 40    40.65Veova � 10      39.8     --       --    --    --Trigonox � 425      5.4      5.2      3.2   5.4   --Solvesso � 100      1.5      1.7      2.2   1.5   2Trigonox � B      --       --       --    --    3.7Part 3Solvesso � 100      1        1        1     1     1Part 4Solvesso � 100      0.4      0.4      0.8   0.4   0.1Trigonox � B      0.6      0.6      0.2   0.6   0.4Part 5Solvesso � 100      0.5      0.5      1     0.6   0.5Part 6Solvesso � 100      1        1        5     --    --n-Butanol  --       --       5.5   1     1Test ResultsSolids     83.8     83       70.8  87.2  90Viscosity  V + 1/2  Z1 + 1/4 H     A     HAcid value 5.5      4        5     4.3   0.2Mn         800      1160     2400  1600  1600Mw         1420     6100     13500 5300  5100______________________________________ 1 Silquest � A151 comprises ##STR10## 2 Silquest � A171 comprises ##STR11##
A clearcoat paint formulated with the copolymer of Example 5 was applied wet-on-wet over a blue commercial basecoat and baked for 30 minutes at 135� C. A transparent solvent--resistant coating was obtained with a gloss of 85, Buckholz hardness of 125 and good acid etch resistance.
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J., Glycidyl Neodecanoate: A Tool for Designing Coatings Resins, Mod. Paint Coatings, 83, 120-6, 1993.* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS6140392 *Nov 30, 1998Oct 31, 2000Flint Ink CorporationPrinting inksUS6255392 *Oct 29, 1997Jul 3, 2001Kaneka CorporationCurable composition for top coating and articles coated therewithUS6539325 *Dec 8, 1999Mar 25, 2003Nippon Paint Co., Ltd.Color matching apparatus for automotive repair paintsUS6544593Mar 16, 2000Apr 8, 2003E. I. Du Pont De Nemours And CompanyHigh solids clear coating compositionUS6592944Mar 16, 2000Jul 15, 2003E. I. Du Pont De Nemours And CompanyHigh solids acid etch and mar resistant clear coating compositionUS6607833 *Mar 16, 2000Aug 19, 2003E. I. Du Pont De Nemours And CompanyHigh solids acid etch resistant clear coating compositionUS6624243 *May 7, 2001Sep 23, 2003Wacker Polymer Systems Gmbh & Co. 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Du Pont De Nemours & CompanyGraft copolymers with segmented arms and their preparation and useWO2003078486A1 *Mar 11, 2003Sep 25, 2003Chung Ding YuPreparation and use of crosslinkable acrylosilane polymers containing vinyl silane monomers* Cited by examinerClassifications U.S. Classification528/32, 524/558, 528/28, 524/590, 525/455, 525/101, 524/588, 524/534, 525/123International ClassificationC08G18/40, C08F8/30, C08F230/08, C09D143/04, C08G18/62, C08F218/10Cooperative ClassificationC08F8/30, C09D143/04, C08G18/6295, C08F218/10, C08G18/4063, C08F230/08European ClassificationC09D143/04, C08F218/10, C08F230/08, C08F8/30, C08G18/40A12, C08G18/62WLegal EventsDateCodeEventDescriptionMay 22, 2007FPExpired due to failure to pay maintenance feeEffective date: 20070328Mar 23, 2007LAPSLapse for failure to pay maintenance feesOct 12, 2006REMIMaintenance fee reminder mailedAug 29, 2002FPAYFee paymentYear of fee payment: 4Oct 17, 1997ASAssignmentOwner name: E. I. DU PONT DE NEMOURS AND COMPANY, DELAWAREFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HUYBRECHTS, JOSEF;REEL/FRAME:008748/0919Effective date: 19970623RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services