Hydrophilic curable ethoxylated silicones

Details Hydrophilic curable ethoxylated silicones Hydrophilic curable ethoxylated silicones

2001-11-15

2003-11-18

Dawson, Robert (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

C528S038000, C528S037000, C106S287110, C106S287160, C427S387000, C556S444000, C556S445000, C556S413000, C556S424000, C428S447000, C442S093000, C442S102000, C442S106000, C442S112000, C442S119000, C525S477000

Reexamination Certificate

active

06649689

ABSTRACT:

TECHNICAL FIELD
This invention relates to hydrophilic, curable, alkoxylated silicone polymers for surface modification and are useful in, e.g., fiber and fabric care, hair care, skin care, pet care, hard surface care, soft surface care, and car care compositions. The compounds are curable silicone polymers which contain one or more polyalkyleneoxy groups, preferably pendant groups, comprising at least some ethyleneoxy units, said polyalkyleneoxy pendant groups are preferably capped with low molecular weight non-reactive capping groups, such as C
1
-C
6
alkyl groups. These compounds are substantive to the surface but keep the surface hydrophilic.
BACKGROUND OF THE INVENTION
Curable silicones comprise silicones having reactive functional groups that can further condense to form higher molecular weight polymers. One type of curable silicones of particular interest is the so-called room temperature vulcanizable (RTV) silicones that typically undergo condensation involving silanol functions. The silanol functions can be produced from other reactive functional groups, usually through reaction with water. Typical reactive functional groups include Si—H, Si—OH, and Si—OR groups, wherein R is typically a low molecular weight alkyl group or an acyl group. Two reactive functional groups of two separate silicone polymeric molecules, usually in the presence of moisture, can condense to form an Si—O—Si bond, thus in effect extending the silicone molecular backbone and forming a new silicone with higher molecular weight. The reactive functional groups can also form covalent bonds with the different surfaces to which the silicones are applied, when such surfaces have suitable functional groups that can react with the reactive functional groups of the silicones. Many curable silicones also contain amine functional groups to provide catalysis for the condensation reaction and/or additional surface substantivity benefit. These properties make curable silicones useful in surface protection and/or modification.
Curable amine functional silicones are broadly used in, e.g., car waxes and polishes to protect, e.g., painted, rubber and vinyl surfaces, such as those disclosed in U.S. Pat. No. 3,960,575 issued Jun. 1, 1976 to Martin, U.S. Pat. No. 3,576,779 issued Apr. 27. 1971 to Holdstock et al., said patents are incorporated herein by reference. Noncurable aminofunctional silicones are also disclosed for use in car care, such as U.S. Pat. No. 4,247,330 issued Jan. 27, 1981 to Sanders, said patent is incorporated herein by reference. Other applications are known. U.S. Pat. Nos. 4,800,026 issued Jan. 24, 1989 and 4,911,852 issued Mar. 27, 1990 to Coffindaffer et al. discloses the use of curable amino functional silicones for fabric wrinkle reduction; U.S. Pat. No. 4,419,391 issued Dec. 6, 1983 to Tanaka et al., discloses the use of curable amino silicones to impart fabrics with softness, slipperiness and sliminess; U.S. Pat. No. 5,098,979 issued Mar. 24, 1992 and U.S. Pat. No. 5,196,499 Issued Mar. 23, 1993 to O'Lenick, disclose noncurable polyethoxylated silicones with polyethoxylate groups capped by cationic groups comprising long chain alkyl groups for use as softener actives; said patents describe various examples of curable amino functional silicones, and are incorporated herein by reference. U.S. Pat. No. 5,091,105 issued Feb. 25, 1992 to Madore et al. discloses the use of hydrophobic curable silicones not containing amino substituents to provide fabric softening benefit in liquid detergent compositions; said patent is incorporated herein by reference.
Typical curable silicones, such as curable amine functional silicones, are surface substantive and make the treated surface very hydrophobic. The surface hydrophobicity is a desired property for some applications, such as car care. A car painted surface treated with curable silicone-containing wax is very water repellent, and causes water to bead up to form distinctive water drops on the car painted surface. This phenomenon is used as a signal for the protection benefit of the wax treatment.
However, the surface hydrophobicity, water repellent property is not desirable in other applications. When a car is treated with curable silicones and then exposed to rain or splashed water on the road, the water drops on the car surface frequently contain dirt and other soils that become visible when these distinctive water drops dry out. This results in nonuniformly soiled spots on the surface that are unsightly and undesirable. On the other hand, a hydrophilic car surface provides a sheeting action with which rain or splashed water can wet and spread across the car surface uniformly, forming a continuous film that is largely drained away and helps the soil run off, or at least spreads the soil more uniformly on the car surface. When the car surface dries out, the soil, if any, is distributed more uniformly, and becomes significantly less visible and more acceptable.
For normal usage, waterproofing of garments and other household fabrics such as towels is also not desirable and should be avoided.
Therefore, it is desirable for many applications, such as in and fabric care, hair care, skin care, pet care, and car care compositions, to have silicone polymers as surface modifiers that keep or make the treated surface hydrophilic. Thus the present invention relates to curable silicones that are surface substantive, but without the accompanying hydrophobicity negative. This surface substantivity results in long lasting benefits, such as fabric color restoration, fabric softening, fabric conditioning, wrinkle control, soil release, and antistatic properties, without the fabrics becoming hydrophobic. It also results in, e.g., long lasting car care benefits, e.g., shine/gloss, color deepening, glide/lubricity, and long lasting hair care benefits, such as shine and easy combing.
SUMMARY OF THE INVENTION
The present invention relates to a class of novel curable silicone polymers comprising:
(a) one or more reactive Si functional groups including Si—H, Si—OH, Si—OR and/or Si—OCOR groups, wherein R is typically a low molecular weight alkyl group;
(b) one or more polyalkyleneoxy groups comprising at least some ethyleneoxy units, said polyalkyleneoxy groups can be part of the polymer backbone, terminal groups (situated at the ends of the silicone polymer backbone), pendant groups, and mixtures thereof, with polyalkyleneoxy terminal and/or pendant groups being preferably capped with low molecular weight nonreactive capping groups, such as C
1
-C
6
alkyl groups, but optionally can be reactive terminal groups, preferably in hindered or protected form that avoid excessive crosslinking prior to application; and
(c) optionally but preferably one or more cationic nitrogen functional groups, being pendant groups, terminal groups, and/or part of the polymer backbone, and mixtures thereof, said cationic nitrogen functional group comprises, e.g., amine functional groups, imine functional groups, imidazole functional groups, imidazoline functional groups; quaternary ammonium functional groups, polycationic groups, and the like, and mixtures thereof.
Each reactive Si bearing a reactive functional group can be either a terminal group or within the silicone backbone. It can also optionally be on a pendant group. Each polyalkyleneoxy group can also be in various positions in the silicone polymer, including: (a) as pendant group linked to the silicone backbone by a linking group, preferably being a hydrocarbon or oxygenated hydrocarbon linking group, e.g., —CH
2
CH
2
CH
2
—, —CH
2
CH
2
—, —CH
2
CH(CH
3
)CH
2
—, —CH
2
CH(OH)CH
2
OCH
2
CH
2
—, -phenylene-CH
2
CH
2
—, and —CH
2
-phenylene-CH
2
CH
2
—, or an aminoalkylene group, e.g., —CH
2
CH
2
CH
2
—N< group and —CH
2
CH(CH
3
)CH
2
—N< group, providing that no O—O or N—O bonds are formed; (b) as terminal group on the silicone, especially linked to the terminal Si atom by the same linking groups listed in (a) hereinabove; (c) as an internal group, incorporated into the main silicone chain by links selected from the linking group

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