Compositions with enhanced flexibility

Patent metadata

Field	Value
Publication number	US-9890303-B2
Application number	US-201715626340-A
Country	US
Kind code	B2
Filing date	Jun 19, 2017
Priority date	Jan 17, 2014
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

Compositions are provided which comprises an active hydrogen-containing resin, a flexibilizer and at least one curing agent. The cured compositions possess enhanced flexibility while maintaining hardness, and are highly suitable for applications such as coatings, adhesives, sealants, gaskets, industrial rubber goods, and the like.

First claim

What is claimed is:

1. A composition comprising:
(a) flexibilizer (i) having the general formula (I):

wherein:
each occurrence of R 1 is independently an alkyl group having from 1 to 6 carbon atoms, a phenyl group or an arenyl group having 7 to 12 carbon atoms;
each occurrence of R 2 is independently an alkyl group having from 1 to 6 carbon atoms;
each occurrence of R 3 is independently a phenyl group or an arenyl group having 7 to 12 carbon atoms;
each occurrence of X 1 is independently a hydroxyl group, an alkoxy group having from 1 to 6 carbon atoms, or an alkoxy group having from 1 to 6 carbon atoms and at least one ether or ester functional group;
each occurrence of X 2 is independently a hydroxyl group, an alkoxy group having from 1 to 6 carbon atoms, an alkoxy group having from 1 to 6 carbon atoms and at least one ether or ester functional group, or a group with the formula (II):

wherein:
R 1 , R 2 and R 3 are the same as defined above;
each occurrence of subscripts a, b, c, d, e and f is independently an integer wherein a is 1 to 3; b is 0 to 500, c is 1 to 500, d is 0 to 10, e is 0 to 50, and f is 0 to 50 with the provisos that
(1) the molar ratio of b to c is from 0:1 to 15:1, and
(2) the molar ratio of d to c is from 0:1 to 1:1;

(b) at least one resin selected from the group consisting of an amine-functional resin (iv), a mercapto-functional resin (v), a resin containing silanol-reacting groups and a resin containing alkoxysilyl-reacting group,

with the proviso that when the resin (b) is the amino-functional resin (iv) or mercapto-functional resin (v), the composition further comprises,
(c) at least one curing agent (vi) selected from the group consisting of isocyanate-containing compound (vii), blocked isocyanate-containing compound (viii) and aminoplast (ix).

2. The composition of claim 1 wherein each occurrence of X 1 is independently hydroxyl, methoxy, ethoxy, propoxy or isopropoxy; R 1 is methyl or phenyl; R 2 is methyl; R 3 is phenyl; b is 1 to 100: c is 2 to 100; d is 0; and the molar ratio of b to c is from 1:1 to 10:1.

3. The composition of claim 1 wherein flexibilizer (i) has a silanol content or a SiX 1 content of from 2 to 15 mole %, based upon the total number of silicon atoms.

4. The composition of claim 1 wherein flexibilizer (i) has a weight average molecular weight of from 500 to 50,000.

5. The composition of claim 1 wherein flexibilizer (i) is HO—Si(CH 3 ) 2 —O—[Si(CH 3 ) 2 O] r —[Si(Ph) 2 O] s —Si(CH 3 ) 2 —OH where r/s is 4, CH 3 O—Si(CH 3 )—O—[Si(CH 3 ) 2 O] u —[Si(Ph) 2 O] w —Si(CH 3 ) 2 —OCH 3 where u/w is 3, Ph is phenyl, and mixtures thereof.

6. The composition of claim 1 wherein amine-functional resin (iv) is represented by general formula (VI):
[H(R 9 )N-] g R 10   (VI)

wherein
R 9 is hydrogen, a linear, cyclic or branched hydrocarbon group having from 1 to 18 carbon atoms, which is optionally substituted by heteroatoms, an alkyl radical which is interrupted by nonadjacent oxygen atoms, an alkoxy group —OR 11 or an acyloxy group —O—C(═O)—R 12 wherein R 11 is hydrogen or a linear, cyclic or branched hydrocarbon group having from 1 to 18 carbon atoms and R 12 is a hydrogen or a hydrocarbon contain from 1 to 18 carbon atoms;
R 10 is a linear or branched polymer group having a number average molecular weight of from 500 to 25,000, as determined in accordance with DIN Standard 55672 (1) using polystyrene standards; and
g is an integer of greater than 1.

7. The composition of claim 1 wherein mercapto-functional resin (v) is represented by general formula (VII):
R 13 SH) h   (VII)

wherein
R 13 is a linear or branched polymer group having a number average molecular weight of from 500 to 25,000, as determined in accordance with DIN Standard 55672 (1) using polystyrene standards; and,
h is an integer greater than 1.

8. The composition of claim 1 wherein curing agent (vi) is an isocyanate containing compound (vii) selected from the group consisting of 1,2-ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4- and 2,4,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate, omega,omega′-diisocyanatodipropyl ether, cyclobutane 1,3-diisocyanate, cyclohexane 1,3- and 1,4-diisocyanate, 2,2- and 2,6-diisocyanato-1-methylcyclohexane, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate, 2,5- and 3,5-bis(isocyanatomethyl)-8-methyl-1,4-methano-decahydronaphthalene, 1,5-, 2,5-, 1,6- and 2,6-bis(isocyanatomethyl)-4,7-methanohexahydroindane, 1,5-, 2,5-, 1,6- and 2,6-bis(isocyanato)-4,7-methylhexahydroindane, dicyclohexyl-2,4′-diisocyanate, 4,4′-diisocyanate, 2,4- and 2,6-hexahydrotolylene diisocyanate, perhydro 2,4′- and 4,4′-diphenylmethane diisocyanate, omega,omega′-diisocyanato-1,4-diethylbenzene, 1,3- and 1,4-phenylene diisocyanate, 4,4′-diisocyanatobiphenyl, 4,4′-diisocyanato-3,3′-dichlorobiphenyl, 4,4′-diisocyanato-3,3′-dimethoxybiphenyl, 4,4′-diisocyanato-3,3′-dimethylbiphenyl, 4,4′-diisocyanato-3,3′-diphenylbiphenyl, 2,4′- and 4,4′-diisocyanatodiphenylmethane, naphthylene-1,5-diisocyanate, 2,4- and 2,6-tolylene diisocyanate, N,N′-(4,4′-dimethyl-3,3′-diisocyanatodiphenyl)uretdione, m-xylylene diisocyanate, dicyclohexylmethane diisocyanate, tetramethylxylylene diisocyanate, 2,4,4′-triisocyanatodiphenyl ether, 4,4′,4″-triisocyanatotriphenyl methane, toluene 2,4-diisocyanate, toluene 2,6-diisocyanate, diphenylmethane 4,4′-diisoyanate, diphenylmethane 2,4′-diisocyanate, p-phenylene diisocyanate, biphenyl diisocyanates, 3,3′-dimethyl-4,4′-diphenylene diisocyanate, tetramethylene 1,4-diisocyanate, hexamethylene 1,6-diisocyanate, 2,2,4-trimethylhexane 1,6-diisocyanate, isophorone diisocyanate, ethylene diisocyanate, dodecane 1,12-diisocyanate, cyclobutane 1,3-diisocyanate, cyclohexane 1,3-diisocyanate, cyclohexane 1,4-diisocyanate, methylcyclohexyl diisocyanates, hexahydrotoluene 2,4-diisocyanate, hexahydrotoluene 2,6-diisocyanate, hexahydrophenylene 1,3-diisocyanate, hexahydrophenylene 1,4-diisocyanate, perhydrodiphenylmethane 2,4′-diisocyanate, 4,4′-methylenedicyclohexyl diisocyanate, tetramethylxylyl diisocyanates, biuret dimers and the isocyanurate trimers thereof.

9. The composition of claim 1 containing from 1.0 to 98 percent by weight resin having an active hydrogen (ii) based on the total weight of the composition, from 0.1 to 80 parts by weight flexibilizer (i) based on one hundred parts of resin having an active hydrogen (ii), and from 0.1 to 90 parts by weight curing agent (vi) based on one hundred parts of resin having an active hydrogen (ii).

10. The composition of claim 1 , further comprising at least one additional component selected from the group consisting of catalyst, organic solvent, polysiloxane resin other than formula (I), isocyanate-reactive scavenging agent, water scavenger agent, desiccant, non-silicon-based epoxy hardener, surfactant, colorant, pigment, rheology modifier, plasticizer, extender, filler, reinforcing agent, adhesion promoter, hydrocarbon resin modifier, UV stabilizer, wetting agent, flow and leveling additive, thixotrope and defoamer.

11. The composition of claim 10 , wherein the catalyst is at least one member selected from the group consisting of organic tin, zirconium complex, aluminum chelate, titanic chelate, organic zinc, organic cobalt, organic iron, organic nickel and organobismuth, amine catalyst, dibutyltin oxide, dimethyltin diacetate, dimethyltin dilaurate, dimethyltin dineodecano

Assignees

• Momentive Performance Mat Inc

Inventors

• Kondos Constantine
• Jiang Ping
• Wusik Martin
• Kumar Vikram

Classifications

• C08G18/61 Primary

  Polysiloxanes · CPC title

• C09J125/14 Primary

  with unsaturated esters · CPC title

• C08G77/16

  to hydroxy groups · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G77/18

  to alkoxy or aryloxy groups · CPC title