In-mold coating compositions suitable as is for an end use application

• US 5,777,053 A
• Filed: 01/17/1997
• Issued: 07/07/1998
• Est. Priority Date: 01/17/1997
• Status: Expired due to Term

• Current Assignee: Omnova Services Incorporated
• Original Assignee: Gencorp Incorporated
• Inventors: Sullivan, Brian J., McBain, Douglas S., Shanoski, Henry, Cobbledick, David S.
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): CHENG, WU C
• Application Number:
  US08/785,514
• Time in Patent Office: 536 Days
• Field of Search: 526/301, 526/329.2, 526/347, 425/542
• US Class Current: 526/301
• CPC Class Codes: B29C 37/0028 In-mould coating, e.g. by introducing the coating material into the mould after forming the article
• CPC Class Codes: C08F 290/067 Polyurethanes; Polyureas
• CPC Class Codes: C08G 18/42 Polycondensates having carboxylic or carbonic ester groups in the main chain
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen

Abstract

An in-mold coating composition for a fiber reinforced plastic comprises an aliphatic resin such as a saturated aliphatic ester intermediate polyurethane having terminal acrylate end groups, a saturated (cyclo)aliphatic (meth)acrylate such as isobornyl acrylate, a hydroxyl alkyl (meth)acrylate, a polyacrylate ester of an alkylene polyol, and a vinyl substituted aromatic. The in-mold coating compositions have good end use weather-resistant properties so that there is no need for a subsequent paint coat thereon which heretofore has been required. The paint-free coating compositions can be either clear or pigmented and can contain various additives such as lubricants, adhesion aids, hardeners, and the like.

Claims

1. An in-mold coating composition, comprising;

(a) a saturated aliphatic polyester urethane acrylate, said polyester portion being derived from at least a saturated carboxylic acid or an anhydride thereof and a saturated diol, said urethane portion being derived from an aliphatic saturated polyisocyanate;

(b) an aliphatic or cycloaliphatic (meth)acrylate wherein said aliphatic or said cycloaliphatic group is saturated and has from 1 to 50 carbon atoms;

(c) a hydroxyalkyl (meth) acrylate wherein said alkyl group has from 1 to 10 carbon atoms,

(d) a vinyl substituted aromatic having from 8 to 12 carbon atoms, and,

(e) a polyacrylate ester of an alkylene polyol wherein said alkylene group has from 2 to 30 carbon atoms.

2. An in-mold coating composition according to claim 1, wherein said (a) saturated carboxylic acid or anhydride has from 1 to 15 carbon atoms, wherein said (a) saturated diol contains from 2 to 15 carbon atoms, wherein said (a) saturated polyisocyanate includes a diisocyanate containing from 5 to 18 carbon atoms,

wherein said (b) saturated aliphatic or cycloaliphatic (meth)acrylate has from 2 to 20 carbon atoms,

wherein said alkyl group of said (c) hydroxylalkyl (meth)acrylate has from 1 to 5 carbon atoms, and

wherein said (e) alkylene group of said polyol has from 2 to 10 carbon atoms.

3. An in-mold coating composition according to claim 2, wherein the amount of said (b) saturated aliphatic or cycloaliphatic (meth)acrylate is from about 20 to about 100 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate,

wherein the amount of said (c) hydroxy alkyl (meth)acrylate is from about 2 parts to about 20 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate,

wherein the amount of said (d) vinyl substituted aromatic is from about 10 to about 70 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate, and

wherein the amount of said (e) diacrylate ester of an alkylene polyol is from 10 to 40 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate.

4. An in-mold coating composition according to claim 3, wherein the number average molecular weight of said (a) saturated polyester portion is from about 1,000 to about 5,000,

wherein said (b) saturated aliphatic or cycloaliphatic (meth)acrylate is isobornyl acrylate and wherein the amount thereof is from about 50 to about 80 parts by weight,

wherein the amount of said (c) hydroxyalkyl (meth)acrylate is from about 6 to about 16 parts by weight,

wherein the amount of said (d) vinyl substituted aromatic is from about 20 to about 60 parts by weight, and

wherein the amount of said (e) polyacrylate ester of an alkylene polyol is from about 15 to about 35 parts by weight.

5. An in-mold coating composition according to claim 4, wherein said (a) saturated aliphatic polyester urethane acrylate is prepared from neopentyl glycol, ethylene glycol, adipic acid, isophorone diisocyanate, and hydroxyethyl (meth)acrylate,

wherein said (c) hydroxyalkyl (meth)acrylate is hydroxypropyl methacrylate,

wherein said (d) vinyl substituted aromatic is styrene, and

wherein said (e) polyacrylate ester of an alkylene polyol is a diacrylic ester of hexane diol.

6. An in-mold coating composition according to claim 1, wherein said composition is reacted utilizing a peroxide initiator.

7. An in-mold coating composition according to claim 4, wherein said composition is reacted with from about 0.25 to about 5.0 percent by weight of a peroxide initiator based upon the total weight of all of the ethylenically unsaturated components employed in the in-mold coating composition.

8. A cured, in-mold coating composition, comprising;

the reaction product of

(a) a saturated aliphatic polyester urethane acrylate, said polyester portion derived from at least a saturated carboxylic acid or anhydride thereof and a saturated diol, (b) an aliphatic or cycloaliphatic (meth)acrylate wherein said aliphatic or said cycloaliphatic group is saturated and has from 1 to 50 carbon atoms, (c) a hydroxylalkyl (meth)acrylate, (d) a vinyl substituted aromatic having a total of from 8 to 12 carbon atoms, and (e) a polyacrylate ester of an alkylene polyol wherein said alkylene group has from 2 to 12 carbon, atoms in the presence of a peroxide initiator.

9. A cured, in-mold coating composition according to claim 8, wherein the amount of said (b) saturated aliphatic or cycloaliphatic (meth)acrylate is from about 20 to about 100 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate,

wherein the amount of said (c) hydroxyalkyl (meth)acrylate is from about 2 parts to about 20 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate,

wherein the amount of said (d) vinyl substituted aromatic is from about 10 to about 70 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate, and

wherein the amount of said (e) polyacrylate ester of an alkylene polyol is from 10 to 40 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate.

10. A cured, in-mold coating composition according to claim 9, wherein said (a) saturated carboxylic acid or anhydride has from 1 to 15 carbon atoms, wherein said (a) saturated diol contains from 2 to 15 carbon atoms, wherein said (a) saturated polyisocyanate includes a diisocyanate containing from 5 to 18 carbon atoms,

wherein said (b) saturated aliphatic or cycloaliphatic (meth)acrylate has from 2 to 20 carbon atoms,

wherein said alkyl group of said (c) hydroxylalkyl (meth)acrylate has from 1 to 5 carbon atoms, and

wherein said (e) alkylene group of said polyol has from 2 to 10 carbon atoms.

11. A cured, in-mold coating composition according to claim 10, wherein the number average molecular weight of said (a) saturated polyester portion is from about 1,000 to about 5,000,

wherein said saturated aliphatic polyester urethane acrylate is prepared from neopentyl glycol, ethylene glycol, adipic acid, isophorone diisocyanate, and hydroxyethyl (meth)acrylate,

wherein said (b) saturated aliphatic or cycloaliphatic (meth)acrylate is isobornyl acrylate and wherein the amount:

thereof is from about 50 to about 80 parts by weight,

wherein said (c) hydroxyalkyl (meth)acrylate is hydroxypropyl methacrylate and wherein the amount thereof is from about 6 to about 16 parts by weight,

wherein said (d) vinyl substituted aromatic is styrene and wherein the amount thereof is from about 30 to about 50 parts by weight, and

wherein said (e) polyacrylate ester of an alkylene polyol is a diacrylic ester of hexane diol and wherein the amount thereof is from about 15 to about 35 parts by weight.

12. A cured, in-mold coating composition according to claim 8, adhered to a fiber reinforced plastic substrate.

13. A cured, in-mold coating composition according to claim 11, adhered to a fiber reinforced plastic substrate.

14. A cured, in-mold coating composition according to claim 12, wherein said in-mold coating composition is substantially free of any other layer thereon.

15. A cured, in-mold coating composition according to claim 13, wherein said in-mold coating composition has less than 3 grams per sq. ft. of any layer thereon.

16. A cured, in-mold coating composition according to claim 12, wherein said coating composition has a 60 degree gloss retention of at least 75% of its original value according to SAE J1960 after 1,000 hours.

17. A process for molding an in-mold coating composition onto a fiber reinforced plastic substrate and forming a coating thereon of a predetermined thickness, comprising;

molding said substrate between separable dies which coact in a first fully-closed position to define a mold cavity corresponding in size and shape to the substrate;

allowing said substrate to harden in said cavity;

separating one of said dies from said substrate to provide a first gap therebetween which is greater than said predetermined thickness of said coating;

injecting a metered amount of in-mold coating composition into said first gap, said amount being sufficient to provide said predetermined thickness but insufficient to fill said first gap;

applying molding pressure to said one die to reduce said first gap to a second gap which is commensurate with said predetermined thickness and to distribute said injected material substantially uniformly throughout said second gap and over said surface;

maintaining said pressure while said material bonds to said surface and solidifies sufficiently to permit complete separation of said dies without disruption of the coating thus formed; and

completely separating said dies and removing said coated substrate from said cavity;

the improvement comprising an in-mold composition which includes the reaction product of (a) a saturated aliphatic polyester urethane acrylate, said polyester portion derived from at least a saturated carboxylic acid or an anhydride thereof and a saturated diol, (b) an aliphatic or cycloaliphatic (meth)acrylate, (c) a hydroxylalkyl (meth)acrylate, (d) a vinyl substituted aromatic having a total of from 8 to 12 carbon atoms, and (e) a polyacrylate ester of an alkylene polyol wherein said alkylene group has from 2 to 12 carbon atoms, in the presence of a peroxide initiator so that a cured in-mold coating composition is produced.

18. A process for molding an in-mold coating composition according to claim 17, wherein said (a) saturated carboxylic acid or anhydride has from 1 to 15 carbon atoms, wherein said (a) saturated diol contains from 2 to 15 carbon atoms, wherein said (a) saturated polyisocyanate includes a diisocyanate containing from 5 to 18 carbon atoms,

wherein said (b) aliphatic or cycloaliphatic (meth)acrylate is saturated and has from 2 to 20 carbon atoms,

wherein said alkyl group of said (c) hydroxylalkyl (meth)acrylate has from 1 to 5 carbon atoms, and

wherein said (e) alkylene group of said polyol has from 2 to 10 carbon atoms.

19. A process for molding an in-mold coating composition according to claim 18, wherein the amount of said (b) saturated aliphatic or cycloaliphatic (meth)acrylate is from about 20 to about 100 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate,

wherein the amount of said (c) hydroxyalkyl (meth)acrylate is from about 2 parts to about 20 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate, and

wherein the amount of said (d) vinyl substituted aromatic is from about 10 to about 70 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate, and

wherein the amount of said (e) polyacrylate ester of an alkylene polyol is from 10 to 40 parts by weight for every 100 parts by weight of said (a) saturated aliphatic polyester urethane acrylate.

20. A process for molding an in-mold coating composition according to claim 19, wherein said (a) saturated aliphatic polyester urethane acrylate is prepared from neopropyl glycol, ethylene glycol, adipic acid, isophorone diisocyanate, and hydroxyethyl (meth)acrylate,

wherein said (c) hydroxyalkyl (meth)acrylate is hydroxypropyl methacrylate,

wherein said (d) vinyl substituted aromatic is styrene, and

wherein said (e) polyacrylate ester of an alkylene polyol is a diacrylic ester of hexane diol.